


Muerto en Missouri

by michaelfalls



Series: The Dalís [3]
Category: Supernatural
Genre: Drugs, Inspired by: Vis à Vis and Orange Is The New Black, M/M, Prison, Violence
Language: English
Status: Completed
Published: 2020-10-25
Updated: 2021-03-02
Packaged: 2021-03-08 21:28:17
Rating: Mature
Warnings: Graphic Depictions Of Violence, Major Character Death
Chapters: 7
Words: 38,303
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27193093
Author URL: https://archiveofourown.org/users/michaelfalls/pseuds/michaelfalls
Summary: Three years after the heist on the Diamonds Factory, it’s time for Dean to take the mask off for good and go to prison.
Relationships: Castiel/Dean Winchester, Michael/Adam Milligan
Series: The Dalís [3]
Series URL: https://archiveofourown.org/series/1876024
Comments: 27
Kudos: 10





	1. Day 1: Killer Businessman

**Author's Note:**

> This is the third and final instalment of the "The Dalís" series. Goes without saying, but this one contains spoilers for '126 Horas' and 'Dalí Diamantes'.
> 
> Like before, using the name of a real facility but not using its actual layout. I'm deriving the prison's layout from the one in Vis à Vis | Locked Up (Season 4) and the one in Orange Is The New Black (the first prison).
> 
> Here's the playlist: https://open.spotify.com/playlist/0zKOSoe8jFgE6t5l7fXaxM?si=sPjmaX22TOeT57b7MBvMNQ
> 
> \- Day One

** THE DALÍS **

**Dean Winchester AKA Kansas**  
A street-fighter and two-time heist mastermind who has been married to Castiel Novak for three years

 **Castiel Novak AKA Angeles**  
The world’s best jewel thief who has been married to Dean Winchester for three years

 **Michael Monroe AKA Detroit**  
An expert jeweller and robber who has been married to Adam Milligan for two years

 **Adam Milligan AKA Windom**  
A shoplifter who has been married to Michael for two years and has been working in the medical field

 **Anael Jo AKA Paris**  
A con-woman currently residing in Paris after the first heist

 **Gabriel Novak AKA Santiago**  
A pickpocket skilled in deception who just keeps moving.

 **Meg Masters AKA Vegas**  
A skilled robber currently residing in Madrid, Spain

 **Mick Davies AKA Manchester**  
A former officer with the Metropolitan police who quit after the second heist

 **Jo Harvelle AKA Houston**  
A robber and hijacker who assists with criminal escapes, currently residing in Sioux Falls

 **Crowley MacLeod AKA Berlin**  
Awaiting the death sentence for the murder of Toni Bevell

The good thing about relationships is that we end up forgetting how they started.  
 **Tokio | Silene Oliveira**

**DAY FOUR**

The vision of a wooden crucifix nailed on the wall swims in a haze of searing agony and indescribable horror. Someone's arms are around the body, holding it up but clearly, it's becoming more of dead weight with every second passing.

A man shouts a name, barely audible over the sound of blood thundering, threatening to abandon its vessel. A heart that feels like it's about to explode with a pain that grabs and doesn't let go, not even for a second to catch a breath. It's almost as if the lungs have gone completely useless with the effort it takes to drag in even the most pathetic of gasps. It's even more effort to keep the oxygen within the ribcage.

No more feeling in the hands. The tingling is gone.

A sharp pain bursts in the side, the distant feeling of blood chasing the blade as it's pulled out, and then knees colliding with the ground as people move to stop the rest of the body from following. No faces can be made out — in retrospect, maybe that should be concerning.

It isn't. The eyes close just as hands find the face.

"Hey! Stay with me," someone says, the first words able to be understood. "You _promised_ me. _Look at me_."

Tries. Fails. Closes again.

"Wake up!"

"Where the hell is she?"

"I'm here, I'm— _Oh, fuck_. That's a lot of blood."

"I said wake the fuck up!"

**3 weeks ago**

When Dean said that the Dalís will never go on another heist again, he meant it.

He'd been getting used to a life like this — since the Diamonds Factory, they still met up once a year to check up on one another, but nobody had any crazy schemes to propose anymore. Meg didn't find any more half-assed plans and Dean had nothing lying around. They'd even hosted Adam and Michael's wedding two years ago in a field in Italy; only the Dalís and Adam's mom were there. It was small, but they spent the whole day together, and Dean wished them a peaceful life together.

He and Cas aren't so bad either; sure, sometimes there are the inevitable couple's fights, but they never go to bed angry. Dean loves waking up in the morning to see the ring on Cas's finger, constructed by melted gold from their first heist and a diamond from the second. Sometimes, he can barely believe that he and Cas are here, now. It's hard to believe that six years ago, Cas was pressing a gun into his side and asking him his name.

Last he heard, Charlie started some kind of tech start-up and Dorothy became a bounty hunter for runaway court cases. Gabriel went back to light thievery, wherever the hell he is. He never stays in one place too long. Anael had settled into a relationship with some girl. Ruby, if Dean remembered correctly. Meg still goes on mini-heists, but never anything as large of a scale as the heists she followed Dean on. He and Cas see Sam and Jess every once in a while — Sam and Jess are working at the same law firm right now, though they're trying to get their own firm, Winchester & Moore, off the ground. Sam also finally proposed to Jess a few months ago, in a semi-elaborate set-up with Dean and Cas's help. Adam and Michael lived in some white picket fence place in Detroit, as far as Dean knows. Maybe they moved since he last spoke to them. Dean thinks Mick quit the Metropolitan police.

Dean hasn't heard from Crowley in a while, and Crowley didn't even show up for this year's Dalí gathering. Dean tried to get ahold of him or Rowena but didn't get any response. Cas tried to assure him that they're fine. Dean didn't agree.

He gets his confirmation when Rowena turns up at his door, looking grief-stricken with running eyeliner.

"Rowena," Dean says, stepping aside so he can usher her into his home. "What's wrong?"

“It’s Fergus,” Rowena almost cries. “He’s in prison.”

"What are you—"

Cas comes out in time to hear her explanation as Rowena clarifies, patience wearing thin, “We need to get him out of jail.”

Cas guides her to the couch to sit and he settles next to her. “Alright, calm down. Everything’s going to be fine.”

“Nothing about this is fine!” Rowena snaps. “I don’t want your comfort! I want your help.”

Dean sighs and folds his arms, giving Cas a look. “What do you want us to do?”

“We wouldn’t be in this if you didn’t ask him to join you on your heist.”

“We’re not doing this shit again,” Dean shuts her down accusingly. “Meg already did this guilt-trip crap before and you know what happened? I got shot, I got a heart attack and I died, so whatever it is you’re planning, I’m not gonna be a part of it. I’m not planning anything for you. Do it yourself. I’m not some fucking—just because I was the boss in the heists doesn’t mean I’m responsible for all of you once we get out. What happens to you outside is _your_ problem, not mine, not anymore. Crowley is not my responsibility—”

Rowena interrupts brokenly, “He got the death sentence. He’s dying in just under three weeks.”

That shuts Dean right up. Cas’s face loses all trace of a fight.

“Less than three weeks?” Cas echoes absently, and Dean sits down heavily on the armrest next to Cas.

“Aye,” Rowena affirms. “I’m terribly sorry, boys, but he’s my son, I can’t leave him there to die. Not for something he did for me.”

Dean presses his lips together as he thinks — he promised Cas that he would never do another heist again, but this technically isn’t a heist, right? And, while true that he no longer bore any responsibility for the Dalís the moment they part ways on the escapes, this was different. Crowley was going to get his brains fried in under three weeks. He can’t turn away from that. Crowley is a loyal friend and Dean always knew he had his back during their heists. He could always trust Crowley. Now, he had to show Crowley that his trust wasn’t misplaced.

Quietly, Dean asks, “Where is he?”

“Missouri,” Rowena answers, hope cast over her pleading face. “Potosi Correctional Centre. Are you saying yes?”

“It’s not a yes,” Dean says the moment he catches Cas’s eyes — he’s not angry or upset, he just looks… defeated and tired. “But it’s not a no, either. Ro, you gotta give me a minute to think about it.”

“Of course,” Rowena says.

Cas asks, the first time he’s speaking since Rowena dropped the bomb on them, “What’s he in for?”

“The agent he shot at the Factory three years ago, Bevell,” Rowena explains. “They caught him for her murder.”

“Fuck,” Dean curses, running a hand over his face. He had held out hope that Crowley could have gotten away with it. “How’d they get him?”

Rowena wrings her hands together with stress. “I don’t know, something about ballistics, tracing his pistol… Putting his name out to any bounty hunter who would sell him out.” She watches the way Cas fidgets next to her and Dean being completely still, deep in thought. Hesitantly, Rowena says, “I don’t mean to rush you, but I need to know if you will help me save my boy… I can’t do it alone.”

Cas exhales, quiet yet heavy, and says, “Rowena, we can’t let him die.” Dean looks at him, surprised that he’s saying yes, and Cas has that look in his eyes that say they don’t have a choice. “We’ll help you.”

“No,” Dean immediately says.

Cas and Rowena look up at him and Cas squints at him, trying to understand. “What do you mean ‘no’?”

“‘No’ as in I’m not letting you help,” Dean says. “I’m going to Missouri. You stay in Italy.”

“Dean,” Cas says, his light tone clearly the beginning of anger. “Can I talk to you alone?”

They find privacy in the kitchen where Dean starts talking before Cas can, “Cas, hear me out. _Please_.” Cas gestured for him to go ahead and Dean does. “You’ve already been to prison before, remember? For three years right before I met you. Your name and face are in the cops’ records. You go in there, it’s not gonna be easy. I’m a ghost, I can go in with my Italy name. I’ll be fine, but I am not willing to send you back behind bars.”

“And what if it fails?” Cas asks, challenging. “What if you can’t break out?”

“Then I’m not letting you stay in there with me,” Dean says. “I want you out here, _free_.”

Cas chews on his lower lip, putting his hands on his hips as his gaze casts down to the floor. Italian tiles that Cas and Dean had picked together, tiles Dean has seen almost every day for the past five years and now Dean will be going to prison voluntarily, and he won’t see these tiles beneath his feet.

Cas finally says, “Dean, I can’t… I don’t want you alone in there. Prison is hard. You said it yourself, I was there for three years. I know how things work. It can change you if you aren’t careful, people in there do things they never get to live down just to make sure we get to the next day.”

“I won’t be alone,” Dean assures, trying to get Cas to agree with letting him go alone. “Look, I’ll ask Meg for help. She’s escaped prison before, she’ll know what to do. She’ll make a good plan. And I’ll ask Michael. He was in jail for a long time, he and I will be a team if he agrees.”

“So _Adam_ will be on this mission?” Cas asks, judgement lining his voice as he narrows his eyes.

“Hell no,” Dean immediately rejects. “I’m not letting you or my brothers go to prison.”

“Why? I’ve been there before, I know how to handle myself,” Cas protests.

Dean finally caves and tells him the real reason. “I know you can, I just don’t want you to come because I don’t trust myself to be able to get you home alive!” He pauses to take a sharp breath in. “I’m sorry for raising my voice. Let me start again. Cas, I don’t trust myself to keep you or Adam and Sam safe. You all trusted me in the first one and I got Balthazar, Benny and Bela killed. You trusted me again and then Michael and I fucking died. If _you_ died this time, that’s too much for me.” Quieter, he admits, “Cas, I can’t live without you.”

Cas closes his eyes and draws in a deep breath. He’s silent for moments that stretch too long for Dean’s comfort, and then he says, “Neither can I, Dean. When will you realise that you’re just as important to me? I just don’t want anything to happen to you in there. Why won’t you let me help you?”

He leaves Dean in the kitchen.

“So Adam’s off on business?”

“Yes,” Michael answers, picking up some books off the coffee table so Dean can put his mug down. The books are mostly about business. At Dean’s interested look, Michael explains, “I’ve been thinking about starting a business. I don’t really know what I’ll do yet so I’ve been reading up.”

Dean nods, smiling, “I think you’d be a fine business owner.” Michael offers him a grateful look, and then Dean clears his throat and says, “I have a favour to ask of you.”

Michael pauses, pressing his lips together as he sighs. “I knew this couldn’t just be a social call… What is it now? Because I already promised Adam that I wouldn’t do anything reckless—”

“Crowley’s on death row in Missouri,” Dean says.

Michael straightens up. “For Bevell?”

“Yeah.”

“Shit.” Michael glances out of the window like he’s thinking about every possibility, every outcome, calculating the chance of one or all of them dying. “We can’t let him die.”

Dean agrees, “Exactly. I need your help.”

Michael sighs, shaking his head slightly. “Dean, I want to, but I don’t want to put Adam in danger.”

“We won’t. You said Adam’s not gonna be back until like a month later, right? We’ll be back by then. I only have two weeks or less to get Crowley out,” Dean says. “Adam might not even have to know you left.”

Michael looks reluctant. “I don’t know… I can’t lie to him.”

“Look, if he does find out, then I’ll claim full responsibility,” Dean bargains. “I’m the one who said we should keep it from him. I want to protect Adam as much as you do. That includes making sure he never sees the inside of a jail cell. We’re on the same side here.”

Michael contemplates it — saving Crowley from death row compared to just not telling Adam that he went back to prison while he was gone. Dean can see nine kinds of reluctance about returning to incarceration and keeping it from Adam, so Dean adds, “I won’t have you as a prisoner. You’ll be a CO. I’ll do all the dirty work this time, alright? I’m the one mixing with the dangerous people. I just need you there to look out for me and be my right-hand man.”

Finally, Michael agrees. “Fine, I’ll do it. But we have to tell Adam once we get out.”

“What you do outside the prison’s your business,” Dean says, but he wears a smile. “Thank you, Michael.”

Michael asks, “But are you sure you want to do this? You have never been to prison.”

“I don’t have a choice,” Dean says.

After Michael, Dean caught a flight to Paris and paid Anael a visit. He knew Charlie and a few other Dalís wouldn’t want anything to do with the new mission so he hadn’t bothered with asking. Though Anael had been the first to bolt for the second heist, Dean thought that with a position as a CO where she’ll basically play their eye-in-the-sky, the new Windom in a role of minimal danger, that perhaps she’ll change her tune.

A brunette answers the door. “ _Qui diable êtes-vous_?”

“Uh, I don’t—” Dean falters, trying to remember the scraps of French that Cas had taught him before. “ _Je ne... parle Français_?”

“Oh,” the woman says. “So you’re one of Ana’s Dalí friends?”

“Ruby, who’s at the…” Anael walks up to the door, trying to dry off her hair — she must have just come out of the shower. She pauses when she sees Dean at the doorway and then breaks into a smile. “Dean!”

“Hey, Anael,” Dean greets, walking into the apartment to accept Anael’s hug. “You look good.”

She pulls away, beaming. “So do you.” Gesturing to Ruby, she introduces, “Ruby, this is Dean, he planned all the heists. Dean, this is Ruby, my girlfriend.”

“Good to meet you,” Dean says politely. Ruby nods once in agreement as she shuts the door behind them. Turning back to Anael, Dean marvels, “She doesn’t mind that you were part of the heists?”

“She actually _likes_ the heists!” Anael says excitedly. “So what can I do for you, Dean?”

“Maybe it’s better if we talk about it alone,” Dean says. Anael brings him to her and Ruby’s room and Dean explains everything to her. He gives her a few moments to think about it and ask her questions — _you’re sure that I will come out of this alive? Can you promise me that being a CO is safe? How confident are you at busting Crowley out?_

Dean offers shaky answers at best, but where he can, he tells Anael that he will do everything in his power to make sure her and Michael come out alive.

In the end, Anael agrees to help, and then Dean flies to Spain to find Meg. Meg heard him out and agreed, saying that she owed him. Because she’s wanted in America after her identity was revealed during the first heist, Meg and Dean agreed that she would work on the outside. She helped him come up with a general plan — her advice had been this; make a plan but don’t make it detailed because you can’t anticipate anything that happens in prison.

Without Cas coming along, Dean still wanted someone to be a prisoner with him — all the ladies were out of the question because Crowley is in a men’s prison, and among the men, two were his brothers and he was unwilling to bring them to jail, Ash had gone into hiding after the Factory, Crowley’s in jail, which really only leaves Gabriel.

Gabriel is a surprisingly easy sell; he agreed the moment he heard Michael was coming.

“Do you have a plan?” Gabriel asks.

“You and I are gonna go on a fake heist. We’ll get caught, thrown in jail,” Dean explains. “The warden of Potosi, thank my lucky fucking stars, he owes me a bunch of favours. Back when I was collecting debts for the first heist, I was helping him do a whole bunch of things because I wanted to use my favours to get artillery from him. I found a better guy so I never spent the favours. Well, now I can. One of the favours will be him hiring Michael and Anael as COs. Second favour will be you and I in the same cell.”

“How many of these favours do you have?” Gabriel questions.

“Five,” Dean says. “I want the last three reserved for emergencies.”

Gabriel nods. “Is Cassie coming?”

Dean smiles, but it’s strained. “Nope. Just you and me, buddy.”

Gabriel gives him a ‘yikes’ expression and says, “You know he’s not gonna be happy about this.”

“I know, but what can I do, man? I need to go into the prison to bust Crowley out but I’m not letting Cas go back in there,” Dean says. “So if you don’t have any objections, we need to get to Missouri and get started. Anael, Meg and Michael are ready.”

Gabriel frowns. “Dude, Michael’s boy isn’t coming either?”

“It’s a prison break, Gabe. Not a heist. We can’t afford a big team,” Dean points out. “Are you coming or not?”

“Alright, alright. You run the ship.”

**Monday, 11:04 AM  
** **0 hours**

There’s something so familiar about the way the prison bus shifts them just the slightest bit as it makes a turn on the road, like the way Benny drove them to the Bank of America five years ago. It’s almost laughable, the way Dean wishes he could go back to that moment, when they were so confident and excited, complaining about their mask not being scary enough. Back when they didn’t have three dead friends. Back when Charlie, Cas, Gabriel, Michael and Dean himself hadn’t gotten shot. Back when Adam hadn’t gotten abducted and beaten by corrupted cops.

Back when things were good, and Crowley wasn’t going to be killed in two weeks.

Gabriel sways next to him like he’s bored, looking around the bus. They were the only two new inmates that day, other than one other guy that was being transferred over from another prison. There’s a blonde CO at the front, driving, but Dean didn’t catch her face or name.

“Who’re you?” Gabriel asks conversationally.

The other inmate looks up at him with a raised eyebrow. His hair is grey at the edges and he looks like he barely smiles. “Ishim.”

“I’m Gabe,” Gabriel grins. Ishim doesn’t return the friendliness.

Since Dean was taken off of his legal death since the police’s discovery that he’s actually alive during the last heist, Dean had gone by his Italian name instead for the mission, Dino De Luca. Granted, the only Italian words Dean knows is _si_ , _no_ , _grazie_ and the lyrics to that one Andrea Bocelli song that Ferrero Rocher uses in their classic advertisements, but Dean can just say he moved to America when he was young and never got to learn the language. Cas is way better at this than he is. He’d be able to sell the Dino De Luca act.

But he’s not here. All Dean has right now is Cas’s brother.

“Not much of a talker, ain’t ya,” Gabriel mutters.

“Kiss my ass, bitch,” Ishim returns. Gabriel raises his cuffed wrists and flips him off.

“Gabe, man, just sit tight, okay?” Dean says quietly. “We’re trying to lay low. Go in, do our job, get out.”

Gabriel scoffs. “Alright, fine.”

The rest of the ride is silent until the bus pulls into the prison gates. Dean peers out of the bus’s windows — a guard at the gate has a key that unlocks it, but it’s on a chain with a bunch of other keys and Dean didn’t see which one it was.

It slows to a stop and the driver guard turns around. If Dean squints, he can read the sewn-in name on her uniform over her right pocket — CO L. Monroe. She flips her blonde hair over her shoulder to send them a dirty look as she says, “Home sweet home, boys. Get the fuck outta here.” Two guards outside the bus are waiting for them and the three get off one after the other, walking in single file as the guards lead them.

“Sunders. How was the SHU?” One of the guards asks jovially, though Dean is sure he’s only mocking Ishim.

“Go fuck yourself, Benjamin,” Ishim mutters, and the two guards laugh. The other one, Nathaniel, speaks into his radio, telling them to open gate 1-1.

Gabriel whispers from behind Dean, “Welcome to jail, Dino.”

Nathaniel leads them to the guard on duty and picks up the clipboard, reading off of it, “Sunders back to his cell at D block, De Luca and Novak to C block. Alright, Ben, you take Ishim. I’ll handle the newbies.”

“Just admit you like parading the new assholes around,” Benjamin laughs, though he does shove Ishim in the direction of D block and tells him to get moving.

Dean and Gabriel follow Nathaniel and the guard asks, “Y’all been in here before?”

Gabriel, ever the conversationalist, answers, “Me, I’ve been in for five years. De Luca’s never been, I think.”

Nathaniel scoffs, leading them up some stairs to the second level. “Five years and you still ended up back in prison. What, did freedom get too boring for you?”

“I don’t know, I kinda miss this place,” Gabriel teases.

Nathaniel rolls his eyes and stops in front of an empty cell with two beds, a sink, a desk and a toilet. “This is your new home."

Gabriel grins and still jokes, “I call top bunk.”

“Anyone ever told you you talk too much?” Nathaniel suddenly asks, turning to stare at Gabriel with complete annoyance. Dean looks between them, already beginning to try and size up the guards, and Nathaniel says, “I don’t know what shitty ass prison you were at before where the COs were your fucking friends, but that ain’t here. Here, you’re our bitches. I don’t joke around with pieces of shit. Get in your fucking cell before I give you a shot.”

“A _shot_ just for joking around—”

“ _Gabriel_ ,” Dean cuts over. “Shut the fuck up, man.”

Gabriel shuts up.

Adam grabs the cup of coffee he ordered, mumbling a quiet 'thank you' as he blows on the surface of the drink. He had an operation to get to in two hours so some caffeine is more than welcome. To his complete relief, the hospital itself had a coffee shop so he didn’t have to travel to get some.

His phone rings and he grumbles under his breath, putting the cup down on a table and pulling his phone out of his coat — Michael. He picks up, saying, “Hey, babe. What’s up?”

“ _Adam, how’s work?_ ”

“Good, yeah. Got an op in two. Just got some coffee,” Adam says, grabbing his cup and leaving the coffee shop. “Did you need anything?”

Michael’s tone sounds strange when he answers, “ _Nothing, I just called to let you know I’ll be out of touch for a while. I’m not sure how long, but I should be back in less than two weeks._ ”

Adam frowns, stopping in the hallway. “What? Where are you going?”

“ _I need to help Dean with something_ ,” Michael says vaguely. “ _I’ll be home soon, probably before you. You won’t even notice I’m gone._ ”

“Wait, what does he need help with?” Adam pushes. Not that he doesn’t trust Dean, but Adam really isn’t all that jazzed about the idea of Michael going on another heist with Dean, especially when Michael got shot and Adam got beaten up by cops the last time. “Michael, please tell me.”

“ _It’s nothing bad_ ,” Michael says. “ _I’ll keep him out of trouble._ ”

Adam chews on his lower lip nervously. “That’s exactly what I’m worried about, Mike.”

“ _Sweetheart, I’ll be fine, okay? Promise_ ,” Michael says, trying to convey all the sincerity in his body. “ _I’ll try my best to call you when I can._ ”

Adam starts to worry, “And how long do I not hear from you before I start to get panicked and call someone? How will I know you’re okay? You might have forgotten but every time you and my brother get together—”

“ _Adam, I promise I’ll be fine_ ,” Michael cuts in. “ _I love you_.”

“I love you too,” Adam replies, still unsure. Michael hangs up then and Adam stands there in the hallway as two nurses walk past, discussing some patient upstairs, thinking about it all. He trusted Dean, surely he wouldn’t put Michael in any danger, not after all he did for him the last time —

Adam didn’t trust Dean at all.

**Monday, 1:52 PM  
** **3 hours**

Dean hasn’t spotted Crowley yet and it seems like Gabriel is coming up empty too. He thought that perhaps death row inmates are kept in a separate cell block — he asked Anael to check it out but he really hoped not. He’d probably have to get himself on death row too to get to Crowley then, and that plan is too risky. If he can’t find a way out of there, then they’re both dead.

Dean cashed in his first two favours and Michael and Anael walk into the prison, donning blue CO uniforms with black pants and shoes, a radio perched on their shoulders. By then, it’s lunchtime, and he and Gabriel are sitting across from each other at one of the tables with the slop they call food. He’s sure the chef inmates are trying their best, but Dean really misses outside food.

Anael’s first shift happens to be in the cafeteria so she casually walks around until she ends up by Dean and Gabriel’s table. There, she says only for the two of them to hear, “I’m gonna be doing surveillance shift from 5 to 9, Michael has it from 1 to 5.”

“Alright. Tonight at 10, I’ll be in the laundry room. We need to figure out all the places with cameras and all the places we can get the hell out of here by,” Dean says, staring down as if talking to his food.

Anael nods and asks, “Where’s Berl—Crowley?”

“Haven’t found his cell yet,” Gabriel replies. “Maybe he’s in a different block.”

“Then I will check it out,” Anael says and then walks off, not wanting to stay there too long and raise suspicions.

Gabriel leans across the table, lifting his fork as he talks. “What if Crowley’s in a different block from us?”

“Then I’ll figure it out,” Dean assures.

Michael settles in the surveillance room, looking over all the aged monitors as the images flicker. He keeps note of the angles of the cameras, how much ground each one covers and which corners are hidden from view. It may be helpful.

He looks at the guards in the cameras — two guards joking around, their name tags close enough to the camera for him to identify them as COs Uriel and Nathaniel. He manages to find a list of the COs in the prison and mentally checks off names with faces until he gets to a blonde CO that walks in from the gate into the plaza. Her face is a bit grainy with the distance it’s at from the camera so he refers to the list again. When he finally finds the CO’s picture, his pen freezes an inch over her name.

_Lilith Monroe — correctional officer, driver. Formerly military personnel._

“Oh, fuck me.” Michael blinks hard and reads it over again. Lilith Monroe.

In the camera, she makes some comment to one of the inmates that he can’t make out since the footage has no audio, but the inmate scoffs at her. Michael puts the list back into the drawer, trying to think of what to do.

Of course, Dean just had to not show him the list of COs working at this prison. Of course, he had to make sure they didn’t all know everything. What, did he want to make himself indispensable or something? Michael throws a pen at the wall in frustration and the plastic cracks loudly, breaking into two pieces on the floor.

A CO walks in then with a flash of what he assumes is either tea or coffee — she’s a redhead with gentle green eyes that Michael recognises from the list as Anna Milton, and she looks at the pen on the floor. “Did you do that?”

“Sorry,” he says insincerely.

“It’s okay. First days can be annoying,” she says, sitting down next to him. “You’re one of the new hires, right? I’m Anna Milton.”

“Michael Milligan,” he answers, wishing and wishing that his real last name didn’t have to come back.

**Monday, 4:25 PM  
** **5 hours**

Michael walks up to Dean’s cell, saying into his radio, “CO Jo, I need to see you in 275.” Bringing his hand down from the radio on his shoulder, he stops in front of the cell and waits for Anael to arrive.

Dean asks quietly, “What’s going on?”

“There’s a big problem,” Michael replies, and then Dean realises Michael is angling his head away from the security cameras in the area.

Anael arrives soon after, throwing one of the inmates a disgusted look when he makes a crude gesture. She mutters, “I hate being here.”

“I’m sorry,” Dean says sincerely. “I’ll try to figure this out as fast as I can. You’ll be back in France in no time.”

“I better,” she replies, walking into the cell with Michael. “Now why did you call me here?”

“I know one of the COs,” Michael admits.

Anael and Dean pause and she asks what Dean is thinking. “Which one?”

Michael casts his glance to the concrete floor. “Lilith Monroe.”

While Dean processes that, Anael says, almost like she knows Dean’s about to lose it and is trying to keep the peace with a joke, “Judging from the name, I’m guessing she’s not an ex.”

Michael hesitates and finally confesses, “Lilith is my sister.”

“You have a _sister_?” That gets Gabriel sitting up and Anael startles at the sudden sound, not having known that Gabriel was there. She flips him off. “Dude, I did not know that.”

“You know, a CO sister would have been useful to know about _before_ I put you as her coworker!” Dean hisses, aware that he has to be quiet.

“If you told me who the COs were beforehand, I would have pointed her out!” Michael refutes.

Gabriel, irritated by the oncoming argument against Michael, interrupts to point out, “Dean-o, you’re sure making a lot of noise for someone whose brother was the inspector on the first heist.”

Dean doesn’t have a good argument for that, he had to admit, and he just sighs and asks, “Does Adam know you have a sister?”

“Does it matter? He’s not here,” Michael snaps.

“Oh, so this is a _secret_? Why the hell did you not tell anyone about her?” Dean asks and Anael throws her hands up in exasperation at them, though it’s obvious that Lilith’s relation to Michael is bothering her now that it can be detrimental to the plan.

“I didn’t think it was important to the mission!”

“Well, clearly, it is!”

Anael rolls her eyes and says harshly, “Don’t act like he’s the only one who fucked up. You forgot to ask Warden Roman for the people in solitary, didn’t you?”

Dean exhales through his nose, already feeling riled up. “What now?”

“John Winchester comes out of solitary some time from tonight to tomorrow morning,” Anael says.

Dean freezes. “Oh, fuck me.”

“This next one, you won’t be happy about.”

“What’s worse than his sister and my dad being here?” Dean asks, brain working a thousand miles a second trying to think about how to ration his remaining three favours with Roman without wasting them all on Lilith and John.

Anael says, and at this point, it’s just rubbing salt on the wound, “And Crowley’s gonna be in the SHU until our third day here.”

Dean has to stop himself from kicking the desk.

Michael runs a hand through his hair and says, “Look, forget it, alright? There’s nothing we can do now but work with what we have. What’s the plan, Dean?”

 _Breathe in, breathe out_ , Dean thinks to himself, shutting his eyes for a second. Anael sees a CO look over at them and nudges Michael and the two move to pretend to search the cell. _You need to keep your cool or you’re never gonna see Cas again._

Dean says, “You just act natural with your sister. Reconcile or whatever.”

Michael lifts up the mattress on Dean’s bed to look under it as he says, “I can’t do that.”

Deep breaths. “Why the hell not?”

“If she knows I’m here, she’ll stop at nothing to kill me,” Michael explains, letting the mattress fall back onto the metal bed frame. Anael, Gabriel and Dean all regard him with wide eyes, and Michael continues, “Why do you think I never told Adam I have a sister? She’s fucking crazy. She thinks it’s some God-given mission to kill me. That’s why I ran off and dropped my last name.”

Dean nods, at his last nerves, and says sarcastically, “So now we have a trigger-happy God squad CO. _Great_.” _Think, Dean. You need a plan now._ He chews on the end of his thumb as he racks his brain for any ideas. “Is the bus the only transport in and out of the prison?”

Anael answers, “Brings in new and SHU-released inmates since SHU’s a different block. Only other transports would be an ambulance but that comes from Washington County Memorial Hospital. On-site, you just have that bus.”

“A CO drove that, her name was…” Dean snaps his fingers, trying to bring the name tag back into his memory. He almost wants to scream when he remembers who it is. “Mother-fucking Monroe.” He considers it for a moment and then asks, “How do we feel about me getting someone outside to sabotage the bus?”

“Who, Jo?” Gabriel questions.

Dean affirms, “Her or Meg.”

Anael scrunches her nose as she gestures for Gabriel to move so she can look under his mattress. “Can you workshop that a bit?”

“No, yeah, you’re right,” Dean submits. “No fucking way I’ll be able to luck out and get all of us on that bus at the same day without other inmates on.”

Anael grabs Dean’s arm and drags him to a corner of the cell to talk in private. Once they’re alone, Michael and Gabriel at the other side of it, she says in a hushed voice, “We’re not trying to break everyone out. _One_ guy only, that’s all I agreed to.”

Dean rolls his eyes. “Well, what do you want me to do? I need someone on that bus and Michael can’t go to Monroe or she’ll fucking kill him.”

Anael glances at Michael and looks him over. “He could take her on.”

Dean stares at her. “That’s my brother’s husband, Anael.”

She levels him a look. “Collateral damage.”

Dean echoes in disbelief, “ _Collateral?_ ” At Anael’s shrug, he says seriously, “This is not some ‘a life for a life’ shit. You do not want to piss off someone who knows at least six ways to kill you and get away with it.”

Anael asks, “Are you talking about Adam or Michael?”

“One of them’s actually killed someone before and he sure as shit didn’t get thrown in jail for that. The other one’s a practising doctor who knows every chemical like the back of his hand. Pick your poison,” Dean says. “And they’re my family too, you know. When I get a plan in motion, you better follow it. You go off-book and get Michael killed, I’ll return the favour.”

Anael laughs in his face, a sharp sound like a slap in the face. “You? Kill _me_? Dean Winchester, you have never killed a person in your life. If Michael said that to me, well, that’d intimidate me, but _you_? I’ve killed, Michael’s killed, but you haven’t. You don’t scare me, Dean.” She turns away from him and shouts out of the cell that it’s clear before she gestures at Michael to leave the cell with her.

Alone, Gabriel says, “Hey, I know we’re all anxious because of Crowley but you’re really tense—”

“I need Cas,” Dean finally breaks. “This is pathetic. We’ve barely been here five hours and I just want him with me. He always—Cas keeps me _here_ , you know? There’s no Kansas without Angeles. I know I told him I want him to stay in Italy, and I don’t regret it, but I… I don’t think I could have kept my cool the way I did in the heists without him because Cas is my fucking rock. And all I have now is you, that redheaded con-woman and a killer businessman.”

“Thanks,” Gabriel says sarcastically.

“You know what I mean.”

“Yeah,” Gabriel mumbles. “Cassie’s a real solid kid. I miss him.”

Dean nods in agreement and pushes all thoughts of his husband to the back of his mind. He had bigger problems in his face right now and as long as Cas is in Italy, out of prison, Dean doesn’t have to worry about him. “Alright, so I have three favours left with Roman. If I spend one to get Crowley out of the SHU tonight and another to put Lilith and Michael on separate shifts…”

“You know, I think Michael’ll be fine,” Gabriel says. “He’s a strong guy.”

Dean admits something he hadn’t even thought about before, “Gabe, I honestly think Adam will pick Michael over me. I don’t want to find out if that’s true. I can’t risk anything happening to Michael. I was the one who told him not to tell Adam that he’s here. If I get him killed…”

Gabriel nods, thinking it over, and then, quietly, asks, “You don’t have a plan, do you?”

Dean doesn’t want to lie, so he doesn’t say anything.

Castiel fucking hates Italy now that his husband is in prison in America.

He’d respected Dean’s wishes to not tell Sam and Jess where he was and what was going on, but they’re beginning to see through Cas’s façade and he desperately wanted to leave, catch the first flight to Missouri and go straight to jail.

And then his phone rings with a call from Adam.

Well, fuck. Dean didn’t tell him he couldn’t tell Adam, so to hell with it. Castiel accepts the call and instantly, Adam asks, “ _Where’s Dean?_ ”

“Missouri.”

“ _Why?_ ”

“Crowley’s on death row and Rowena asked him to help rescue him,” Cas answers.

Adam pauses. “ _So you’re telling me that Michael is in_ prison _?_ ”

“Michael is working as a guard, according to Dean,” Castiel fills in. “He should be safe.”

Adam considers the new information for a grand total of 0 seconds before he says, “ _I don’t care if he’s a guard or an inmate. Cas, come on. Sneak me into the prison. I can be a nurse, you can be some, I don’t know… chaplain?_ ”

An opportunity, Cas realises, has presented itself. He asks, “Are you sure? I think Michael and Dean were adamant that you never see the inside of a prison.”

“ _Who else is with them?_ ”

“Anael and Gabriel,” Cas answers.

“ _Okay, then no offence, but I don’t trust any of you to bring Michael back alive from jail_ ,” Adam says frankly. If there’s anything Cas always respected about Adam, it was that he had little to no regard for feelings when it came to telling the truth. “ _Either you go in with me or I go in myself._ ”

Castiel nods. “Alright, fine. I’ll meet you in Missouri. But Michael won’t be happy to see you.”

“ _And I remember explicitly telling Dean to leave Michael out of any future crazy things that can get him killed but here we are._ ”

**Monday, 9:56 PM  
** **10 hours**

Dean, with careful watching and estimation of the cameras, finds a spot that’s surely out of camera range and waits for Michael and/or Anael to show up.

Eventually, about six minutes after Dean reaches, Anael appears. “John’s gonna be here any minute now.”

“What block is he in?”

“C block.”

“Of course,” Dean sighs. “What if I cash in a favour to extend his solitary stay?”

Anael thinks it over and says, “You could, but you could also just ignore the guy.”

“He’s my dad! I can’t avoid him forever,” Dean points out.

Anael nods, seemingly in understanding until she says, “If you’re gonna keep John out until you leave, then you’ve gotta do the same for Michael and the Hand of God to keep the peace and I know you don’t have enough favours to spare for that, so Johnny’s staying.”

Dean smiles, plastic. “I see why the black market fucking loves you.”

She grins with just as much falsehood and says, “I’ll talk to the head guard and see if I can make changes to Michael and Lilith’s shifts. That’s done. Now I want you to tell me what the plan is.”

“We need to work out all the logistics first before I can make a plan,” Dean explains. “I need guard schedules, when do shift changes happen, figure out which inmates or guards can be of any use, make sure my dad doesn’t screw things up when I see him tomorrow… It’s a lot, Anael.”

She leans in close and says, “Michael and I will work on what we can and get back to you. You better have a semi-stable plan by tomorrow or getting Crowley off death row and running from Adam and Michael are the least of your problems.”

With that, Anael walks off, leaving Dean alone in the laundry room.


	2. Day 2: Blackjack

**Notes for the Chapter:**

> CW/ Mentions of drugs

**2 years ago**

"Big day."

“Yeah,” Michael says with a faint smile. Dean walks up to join him at the brink of the field overlooking the setting sun.

Dean closes his eyes and basks in the gentle warmth of the horizon, breathing in Italian air and listening to the sound of Anael and Charlie trying to convince one to let the other pass the ring to Adam and Michael when it’s time. He opens them again and turns to see Michael looking at the sunset. He asks, “So you’re taking Adam’s name, huh?”

“Yep.”

“Not Winchester?”

“I’m not marrying you, Dean,” Michael jokes, and Dean elbows him.

Laughing, Dean says, “Michael Winchester doesn’t even sound that good anyway. Michael Milligan’s better.” Michael hums in agreement and, after a moment of consideration, Dean asks, “What was it before this anyway?”

Michael raises an eyebrow. “What?”

“Like now, you’re Michael Milligan and before, I only knew you as Detroit and then just Michael. What was your last name before?” Dean clarifies.

Right then, Adam comes up behind them and says, “It’s not that important.”

“Hey, babe,” Michael smiles softly, leaning over to press a quick kiss to Adam’s lips. “Yeah, it’s not that important.”

Dean tilts his head as a way of seeing their point — some of the Dalís wanted to leave a part of their past behind and the others wanted to go back to it. Dean knows his life before with Bobby, Ellen, Jo and Sam, it was good. If he was honest with himself, he preferred that peaceful life compared to the one he got himself with the heists.

If he could go back in time, he probably wouldn’t have done the heists. If he had known what it would cost them all, he wouldn’t have — and yet, seeing them all so happy getting ready for the wedding, seeing Michael and Adam reunited, it seems almost worth all the trouble.

“Okay, Michael Not That Important,” Dean teases and Adam rolls his eyes before pulling Michael back with him to where the others were. Dean turns to watch them go — Crowley pops a bottle of champagne and Meg curses at him when the cork almost hits her. Sam and Jess laugh when they get a bit of champagne on themselves and they kiss, and Cas waves at him to join them.

Dean waves back to say he will, then he looks out at the view again, spreading his arms as if welcoming the sun.

“Dean!” Sam shouts across the field. “We’re gonna start soon before it gets too dark!”

Dean smiles, drinking in the view of this family they’d made, painted in soft lilacs and ambers of a setting sun.

**Tuesday, 9:03 AM  
** **22 hours**

Castiel follows the CO, Anna Milton, down the corridor as she tries to direct him to the in-prison chapel. Two inmates walk by — they’re pretty small in frame, so Castiel doesn’t think they’re in for anything big, maybe something simple like counterfeit or scams — and they stare at his priest outfit.

Anna notices them and reassures, “Don’t worry. Religion isn’t too big a thing here. If they aren’t interested, they’ll probably just leave you alone.”

“I’m not worried,” Cas replies. She turns a corner and stops outside the chapel. It’s small with an altar and two columns of dusty mahogany benches, five rows each. Wide-eyed, he comments, “Nobody’s been here in a while.”

The corner of her mouth quirks up in a half-smile. “No kidding. I know there’s some believers around the prison. There’s always believers, you know. Oh, that CO, Lilith. She’s super into the God thing.”

“And you?”

“I have faith, but not as much as some others,” Anna answers. She walks into the chapel with Cas and says, “Well, if there’s nothing else, I’ll leave you be. There’s signs on the ceiling if you want to find your way around, but I’ll be directly upstairs if you need me.”

Cas smiles. “Thank you.”

Once Anna disappears down the hallway, responding to a call on her radio about a fight in B block, Cas slips out of the chapel and follows the signage nailed on the ceiling to the medical bay. There’s about five beds there and one office for the main doctor, assuming that there were no other correctional nurses and that the doctor only gets additional help from inmates who knew what they were doing.

A man stands there in a white coat, looking over some documents. He looks up as the door clicks when Cas opens it and greets him with a warm smile once he sees the outfit. “Hey there. You must be the new chaplain. The old one got let go for smuggling in drugs.”

“I see,” Cas says, shutting the door behind him. Behind his back, his fingers find the lock and he speaks over the sound of it clicking, “You’re Dr. Turner? I saw your name on the list of employees.”

“That’s me. You must be Clarence,” Rufus confirms, putting down the documents. Cas nods — he had decided to go by a different name in there, just like how Dean went by his Italian alias. “How may I help you?”

“I’m just taking a walk around, getting acquainted. There aren’t really any inmates who know the chapel’s open again so I’m basking in the peace,” Cas says. Rufus chuckles as if he gets what Cas means. “Are you the only one working here?”

Rufus nods. “Yep. Just me. Sometimes, an inmate will come help.” So Cas was right in assuming that, then.

He walks over to stand closer to Rufus, asking, “Would you accept more help? I know someone, a professional.”

Rufus considers it. “Well, gang activity in the prison’s been escalating a little lately. I think it wouldn’t hurt to get an extra set of hands ‘round here. If you can swing this by Roman, I don’t mind him coming in tomorrow. Though I gotta warn you, kid. Roman’s pretty tight with his money.”

“He doesn’t mind working for free,” Cas offers. Adam really wouldn’t — with the combined shares of him and Michael from the second heist plus his own from the first, Adam could work for free for the rest of his life and it wouldn’t matter.

“Then the warden should be fine with it,” Rufus says. “Who’s your friend?”

“Adam Milligan,” Cas answers. “I’ll talk to Roman. He could come in after lunch.”

Rufus seems to lighten up at that. “Perfect. Can’t wait to meet him.”

Dean didn’t get much sleep last night. He’d stayed up trying to think of a plan like Anael asked him to.

He ran over everything in his mind again and again — John will be out of solitary in less than an hour, Crowley will be out tomorrow morning. Michael’s sister has to be kept apart from him. The bus is driven by aforementioned sister. He needs to get himself, Gabriel and Crowley out, the rest simply didn’t have to come back to work the next day.

Meg’s plan, loosely based on the one she used for her own break out, went like this — an inmate drove the van so she simply knocked the original driver off their duty with unscrupulous means and took over. While the guards got out to get the ad-seg inmates, she got out, put a brick on the gas and jumped out. They’d chased the van thinking she was driving it away when in reality, she was halfway through the thick of trees near the solitary block. By the time they realised the van had no driver, she was already gone.

Of course, it seemed like a good plan until they came to Potosi Correctional Centre and discovered that Michael’s correctional officer sister is the driver of the bus. It’d been scrapped the moment they got on the vehicle.

They had a cell-phone that Anael brought into the prison for them and left in the interiors of their hollow steel bedposts. Dean relayed all the new information to Meg when it was an hour past lights out and together, they tried to readjust the plan as such:

If Lilith was truly as awful as Michael makes her out to be, then surely using underhanded ways to get her off bus duty wouldn’t be a hit on anyone’s morals. After which, they’ll just take the bus and go. If there are other inmates to be fetched or brought, just leave them behind. Dean complained that they’ll be caught instantly if they didn’t bring anyone else but Gabriel, Dean and one death row inmate. Meg reluctantly agreed and the plan got scrapped. Then Meg had suggested them going to the SHU and getting bust out from there instead. Dean thinks it’s too risky.

By the time morning comes, they’d bounced idea after idea between each other and ended up with just as much of a plan as when they started — barely anything.

Dean hides the phone in the bedpost again just as Gabriel blinks himself awake, the morning alarm waking them up. “Morning, Gabe.”

“God, I forgot how bad the sleep was in here,” Gabriel mutters, already rummaging for his morning supplies. “Did you get any rest?”

“Nah, was thinking.”

Gabriel nods lazily, looking through his supplies to get the toothbrush. “Any luck?”

“Hopefully, today doesn’t bring any more surprises and I can sit down and finalise it. Maybe I’ll get a clearer view with some food in me,” Dean says. Gabriel nods, unconvinced that food will be enough to get his brain going, but he leaves him to go to the bathroom to wash up.

Michael stops outside his cell, arms folded. “Hey, Dean.”

Dean gives him a forced smile. “Mornin’. You look grumpy, did Adam call you last night?”

“No,” Michael answers, looking down the hallway at inmates walking by. “I came by to tell you that Anael will be collecting your father in a bit from the bus. I think she already told you that he’s in the same block as you. What are you going to do about that?”

“I’m gonna avoid him as best as I can,” Dean answers. “I told Anael to try and suss out his habits. You know, his hangout spots. I’ll just stay away.”

“We can’t hide forever,” Michael points out. “At some point, John will know you’re here, the same way Lilith will know I’m here.”

“And I will deal with it when it comes to that. The plan is the priority right now,” Dean says. The last thing he needs is his teammates getting panicked about him not having a plan on their second day in jail. He doesn’t need one to decide to feed the rest of them to the sharks to save their skin. With being in prison, surrounded by inmates who are willing to kill you for drugs or even just for looking at them the wrong way, he’s aware tensions are higher than they have ever been during the heists. He didn’t want to worsen it. The best he can do is pretend he knows what he’s doing until he actually does — fake it till you make it, as they say.

Michael sighs but nods anyway. “Alright. De Luca, get moving. Breakfast’s in half an hour.” With that, Michael leaves down the hall as his radio crackles to life — something about an inmate from D block.

Dean gets his supplies and goes to the main bathroom, wanting to take a morning shower — it’s gross, to say the least. Even with multiple bathrooms all around, it’s still crowded and some aren’t even dressed modestly. Dean ends up deciding to forgo the shower and just brush his teeth in his cell.

At breakfast, he finds Gabriel in the cafeteria seated with some blonde kid with a naive look to him. He puts his tray of slop down and nods towards the fresh-faced guy. “Who’s that?”

“I’m Alfie,” the kid answers, grinning.

Gabriel explains, waving the food around on his fork as if it isn’t the most disgusting thing he’s ever seen, “He’s in for running scams. Easy stuff.” He suddenly widens his eyes as if recalling something and leans across the table conspiratorially, “He says Ishim’s in for a _double_ _homicide_.”

Dean almost chokes on his stale pasta. “Double homicide? And you were fooling around with him on the bus?”

Alfie says lightly, “He’s not the worst guy here if you’re worried. I mean, people have been in for worse than that.”

“Worse than double homicide?” Dean repeats. “Kid, you have seen some shit if you think murder isn’t that bad.” Alfie laughs and Dean doesn’t know if that’s unsettling or annoying.

“Maybe,” Alfie says good-naturedly. “I’ve been here for a few months now. You get used to it, I guess.”

“You hear that, Dino? You get used to it,” Gabriel adds unhelpfully.

**Tuesday, 12:36 PM  
** **25 hours**

Anael was asked by the head guard, Bartholomew, to fetch John Winchester from the bus since he’s the only inmate coming in for the morning. She waits for about ten minutes until the bus finally pulls in through the gate. As expected, Lilith is in the driver’s seat, looking bored out of her mind as she stops the bus and cuts the engine. She turns in her seat and orders John to get out of the bus before she does.

While Benjamin guides John out and makes sure his handcuffs are secure, Lilith walks over to Anael, spinning the keychain with the bus key around her finger. She smiles, saying, “Morning, Jo.”

“Morning,” Anael returns. “Was he quiet on the ride over?”

“Yeah. Think the SHU really did the mother-fucker in,” Lilith says, clearly enjoying it. Benjamin shoves John forward until they stop by Anael and Lilith. Deciding that John can wait a few more seconds, Lilith asks, “Hey, I was asking around. Have you seen CO Milligan?”

Anael lies, “No, why?”

“‘Cause there’s a new guy coming to medical today,” Lilith answers. “Nurse Milligan, right?”

Benjamin nods just as John looks up, squinting in what Anael reads as being surprised. She curses inwardly as the connection sinks in — she’d forgotten that Adam is John’s son too. And here, she thought she’d figured out a way to keep John and Dean apart. Benjamin says, “You think they’re brothers?”

“Dunno,” Lilith mumbles. She cocks her head towards John and says to Anael, “You should go before Bartholomew makes noise about it.”

Nodding, Anael grabs John’s arm and ushers him towards the gate. She says into the main channel on her radio, “Gate 1-1.” The gate opens and she gets him to the front desk to register him in.

As she tries to find his name on the clipboard to note his return to C block, John asks, “Do you know Nurse Milligan?”

Anael looks up at him and taps the pen impatiently against the top of the clipboard. “No. Do you?”

John pauses. “No.”

She locates John’s name and marks him down, saying, “Alright, you’re going back to C block, cell 262.” At least his cell isn’t that close to Dean and Gabriel’s. It should make it a little easier to keep them separate. She gestures to him to follow her and she walks him to his cell where his cellmate isn’t there. On the sheet, it’d said he was with someone called Virgil.

John goes in without saying much else, putting his things down at his side of the cell and busying himself with setting up his bed again. Anael eyes him carefully and glances out of the cell to see if he’ll be able to spot Dean’s from here. She can see Dean’s cell but the interior is practically out of view so it should be fine.

“You walk around often?” Anael asks. Maybe if she can find out his habits, Dean can simply just avoid his spots.

John answers, “Not really, officer. I just keep to myself.”

“Now, that can’t be true. Otherwise, you wouldn’t have been in the SHU,” Anael points out.

“What do you want me to say?” John asks. “I went to the SHU for a fight in the yard. That’s it. I’m not dealing or whatever you’re gonna accuse me of.”

“I wasn’t gonna say that,” Anael mutters, rolling her eyes. “Alright, Winchester. Back to what you were doing. Stay out of trouble.”

Dean decides to go to the recreation room to scope out other inmates that may have any useful skills. While Michael and Anael were assigned to check camera angles, shift changes, which guards were a threat to the break-out, Dean and Gabriel took the responsibility of doing the same with inmates — which spots in prison did they not gather around as much and therefore provided more discretion, which ones were dangerous and rife with inmates.

There, he sees Ishim with some other inmates watching a rerun of a football game from about 6 years ago, if Dean could hazard a guess. There’s some Hispanic inmates at one side talking in Spanish, too fast for Dean to pick out even the simplest of words, and one Chinese guy sitting and reading a magazine, one leg propped on the chair.

Dean picks an empty table and sits, mentally noting that CO Hannah Johnson is on duty at the rec room at this time. One of the Hispanics glances at him and makes a comment where Dean could pick out the words _chico blanco._

Right then, the door of the rec room swings open and Dean doesn’t turn to look, but the man drops a deck of cards on the table in front of him and sits across from him.

“Hey, son.”

“Dad,” Dean mutters, staring at the cards as John picks them up and begins shuffling. “What the hell did you do to end up here?”

“We all do shit when we’re drunk,” John answers vaguely, passing out two cards between them. Blackjack, then. Dean picks up the cards just as John asks, “Your brother, is he here? I heard about the new nurse.”

Dean freezes. “What new nurse?”

“Nurse Milligan.”

Oh, _fuck_. Dean tries not to show any expression on his face at that. “I don’t know anything about that. Milligan’s a pretty common name.”

“Not when he joined today and you just arrived yesterday,” John says. “What the hell is Dino De Loco?”

“ _Luca_ ,” Dean corrects. “My Italian name.”

“You’re not Italian.”

“No shit,” Dean mumbles, taking a card from the top deck since his cards only added up to 15. He gets a 7. “Look, I’d prefer if we just kept away from each other while I’m here.”

John ignores him and says, “My cellmate told me you were in for robbery. I thought with someone like Bobby taking you in, you wouldn’t get caught. Bobby was the master.”

Dean shrugs. “People fuck up. I mean, look at you.”

John eyes him, slowly reaching to get a card. He peers at it and takes another before wincing. “24.”

“22,” Dean says, returning his cards to the deck and John shuffles it once more. He’s sure neither of them is really playing. It’s just a matter of keeping their hands busy. “Did you hear me? I don’t want this to be some regular thing. I know how you treated Sam and Jess while I was gone."

John splits the cards again, two per person, and says, “I thought you died.”

“Everyone did. That was the point,” Dean replies, looking at his cards — 7 and 9. “So are you just gonna keep ignoring me when I talk? Because I will just walk out.”

Finally, John regards him. “I’m not stupid. I already saw you here when I came back. You have that guard you keep talking to, that one with the black hair that I’ve never seen before. You’re gonna bust someone out.”

Dean’s hand hovers over the deck.

John doesn’t look up from his cards, continuing, “Now, I can tell CO Monroe — she’ll gladly take you all down — or you can buy my silence.”

Dean takes the top card off the deck. “I’m not busting you out.”

“It’s that or you get out of prison by tomorrow because I sure as hell ain’t gonna wait longer than that for a real answer,” John says. Dean looks at his card — 5. He puts his cards down and John scoffs, taking back all the cards and reshuffling. As he does so, he talks. “A part of me knew you weren’t dead. But I definitely didn’t think I’d see you again in here.”

“Well, surprise,” Dean says insincerely. John gives out the cards again and Dean checks — an ace and a 10.

“How are you?”

“You don’t get to ask that,” Dean replies, pretending to consider his cards. When Dean makes it clear that he’s not getting more cards, John reaches for another. “I’m not going to get you out. I don’t owe you anything.”

“Think about it,” John says deliberately. “You haven’t done anything yet so I assume you’re just waiting for someone. The only other person with me in ad-seg at the time was MacLeod. I can destroy this in minutes. I’ll give you time to think it over. I expect to hear the plan by tomorrow.”

Irritated, Dean says, “You don’t control me anymore. Not out there, and never in here.”

John looks him up and down as if sizing up his demeanour. “You’ve never been in the slammer before, have you?”

“No,” Dean answers coldly. “But don’t think that means I’m scared to do anything to you. If it comes down to it, I _will_ pick myself over you, and I am not above destroying my morals for that.”

Dean slaps down his blackjack on the table and stands up abruptly, walking out of the rec room.

**Tuesday, 3:52 PM  
** **29 hours**

Michael’s heart plummeted the moment he heard Warden Dick Roman tell them about the new correctional nurse that would be coming in at 4 in the afternoon — Adam Milligan. He waited all morning for the shift change at 4 and asked Anna if she could come to relieve him earlier. She’d agreed, thankfully, and he instantly sets off for the medical office.

He keeps his pace normal but quick as he walks by inmates and guards — CO H. Johnson had given him a strange look as he passed — and when there are no more people around, he speeds up and comes through the door of the med bay, seeing Adam in a white coat. The other doctor, Rufus Turner, doesn’t seem to be around.

As if reading his mind, Adam says, “Rufus went out, he won’t be back until 4:30.”

Michael nods and shuts the door behind him, turning the lock on it so nobody can interrupt them. Now alone, Michael asks, “What are you doing here?”

Adam raises his hands slightly as if trying to calm him down and says, “I know you think I just shit all over the plan but you gotta hear me out, okay?” Michael nods once more and Adam continues, “Just to get you up to speed first — Cas told me what you were actually doing and he got me a job here.”

“How could Castiel—”

“I asked him to. Cas didn’t do anything wrong,” Adam defends. “I just want to know why I had to find out from _Cas_ and not you that you were going to prison. When you said ‘problem’, I expect it to be something like I don’t know, he busted his car. Not going back to prison.”

Michael presses his lips together and casts his gaze down on the linoleum floor. “I’m a CO this time. And Dean asked me to not tell you.”

“Dean’s my brother,” Adam says. “I’m your _husband_.”

“I’m sorry,” Michael apologises sincerely, finally looking back up and running a thumb over the back of Adam’s hand. “Adam, please don’t be mad. I didn’t want you to do anything impulsive but I guess I should have known you’d come in after me. I just never wanted you to know what it’s like in a place like this.”

Adam exhales slowly. “I’m not mad. I know what you’ve done in prison, Mike. Doesn’t change the way I feel about you.” Michael seems unconvinced still, and Adam continues, “If it’ll make you feel better, I’m not gonna be in your way. I’ll be here in the med bay until it’s time to go. I know how to handle myself.”

“I know. You must be the greatest man I’ve ever known,” Michael says. “But I guess I’m just worried about whether we can pull off the plan.”

Adam leans in a bit closer and, even though there’s nobody else there, his voice drops to a low volume as he says, “Dean doesn’t have a plan.”

Michael blinks. “What do you mean?”

“Whatever scrap of a plan he and Meg came up with must have gone to shit by now, right? I mean, Gabriel filled me in; our dad’s here, your murderous sister’s here — which we’re coming back to in a sec — and Crowley’s in solitary until tomorrow. Look at that and tell me you still think he has a stable plan.”

Adam had a point. Michael knew since yesterday that the plan had been destroyed the moment he saw Lilith on the cameras and when Anael told them about John and Crowley, but he had been desperate to not believe that he had walked right into a failed plan and possibly into his next prison sentence while Dean acted like he had his shit together.

Absently, he echoes, “Dean doesn’t have a plan.”

“Look, the only plan we all need to think of is getting Dean, Gabriel and Crowley out. The rest of us just don’t have to show up for work,” Adam says, already trying to organise the work.

“Yeah,” Michael says, distracted. He’s trying to think — Dean has as much of an idea on what to do as they do, which is not much at all. If Dean doesn’t have at least half of a plan by the time Crowley comes back from the SHU, then he may as well be fucked. He can’t avoid Lilith forever, especially when they have some shared shifts. “Adam, I’m not gonna get caught again. I can’t go back to prison, I hated it. And not with all the charges from the Factory heist, I’ll never fucking get out.”

“You won’t go back,” Adam assures, cradling Michael’s face in his hands. Michael kisses Adam’s hand, trying to calm his nerves, but now that he’s accepted that Dean has no plan, his thoughts are chaotic. Adam’s eyes track Michael’s movement and he asks, “Are you okay?”

Michael takes Adam’s hands off of his face and into his own. “I’ll be fine. About Lilith… I never told you about her because I just wanted to leave that part of my life behind. She’s completely delusional. Growing up, she was convinced that God had given her a mission — to kill me. I don’t know why she ever thought… But one time when we were teenagers, she’d almost got me while I was asleep. I woke up in time but I couldn’t take it anymore. I ran off, dropped my last name.”

Adam nods along to show that he’s listening, though he’s clearly concerned about this. “Are you guys on different shifts?”

“Dean wanted to save his favours with Roman in case anything goes wrong so we all agreed that I would just avoid her,” Michael answers and Adam rolls his eyes. In Dean’s defence, Michael says, “He was just making sure we have contingency plans.”

“ _That’s_ what you got from that?” Adam asks, raising an eyebrow. “What I got was that Dean picked three favours with a private arms dealer over your life.”

Michael falters.

Adam confesses, “Listen, I don’t think I trust Dean very much anymore.”

“I thought you and he were on good terms,” Michael says, confused.

“Not when it comes to you,” Adam replies. “We all know he’ll pick Cas over any of us and Cas is in the chapel right now. If this prison thing doesn’t work out, he’ll feed us all to the wolves to get Cas out.”

Michael denies, “That’s not true. He’d pick you too. He didn’t ask you or Sam on this specifically because he didn’t want to get you guys hurt with all the inmates around.”

“Doesn’t matter if he didn’t ask me. He already hurt me when he decided you were expendable enough to bring on the mission,” Adam refutes. Michael doesn’t argue that point — he’d been aware that the last time Adam and Dean met, Adam had told him not to involve him or Michael in anything anymore because they’d agreed that they wanted to live a peaceful life in Detroit. Dean had complied until Crowley got on death row.

“Crowley’s gonna die. I think we can put that agreement aside for at least that,” Michael says.

“I know, I know. I don’t regret coming in here to help him and you,” Adam says. Michael can feel his frustration at the whole situation. “I’m just saying that he could’ve looked for other people, you know? Not that I don’t want to help save Crowley, but still.”

“I get what you mean,” Michael says. “Too late for that now, right?”

Adam huffs a fake laugh. “Yeah.”

Michael glances at the clock on the wall and says, “I need to go, I have a yard shift. Maybe we can talk more later. I’ll come back in here at dinner time and we could eat together, maybe?”

“I’d like that,” Adam says. “Rufus will probably be here but he’s a pretty cool guy.”

“Then I’ll see you when I do,” Michael says, kissing Adam once before he leaves the med bay with a newfound loss of trust in Kansas—

Dean.

Dean didn’t have a mask or a city to hide behind anymore and Michael no longer had faith in the man he was following.

Out in the yard, the sun isn’t so bright now that it’s closer to evening, so Dean has a jacket on over his prison uniform. Gabriel ties the sleeves of his jacket around his waist and has a toothpick between his lips.

“Oh, hey. Ishim,” Gabriel points out.

Dean frowns. “Why do you care so much about that guy?”

“I just think he looks interesting,” Gabriel says. He chuckles slightly as he mumbles to himself, “Double homicide. Would’ja look at that? Who would’ve thought?”

 _I would’ve thought_ , Dean thinks. _Dude looks like a Bond villain._

A bald man with the creepiest expression Dean’s ever seen on a person comes up to them, asking, “You looking?”

Dean narrows his eyes. “For?”

Gabriel elbows him and takes over. “Why, you got some?”

The man grins — Dean decides he doesn’t like him — and says, “New shipment. Fresh blood gets a discount on the first buy.”

“How much are you selling for?” Gabriel asks, grinning, and Dean glares at him pointedly.

“We’ll see what you have and see what you’ll get,” the man answers.

“Who do I look for?”

The man whispers, “Alastair.” His voice sends chills down Dean’s spine.

With that, Alastair leaves, and Gabriel turns to him. “You just met the resident drug dealer.”

“Dude, what the fuck,” Dean mutters. “Did you deal when you were in prison or something?”

“No!” Gabriel denies, offended. “I just thought we should get to know all the big guns here so we know who to avoid. While you were away, I found out Asmodeus is the go-to guy if you wanted stuff snuck in. I think he and Alastair work together for the drug supply but I also think Alastair’s in cahoots with one of the COs. My bet’s Lilith.”

Dean shakes his head. “Jesus. God-crazy killer and a drug dealer? What the hell kind of family does Michael have?”

“A reason why he was so jazzed about taking Adam’s name, I guess,” Gabriel jokes, waving to one of the other inmates. “Hey, you have any cigs? I wanna get some hooch.”

Dean stares at him. “Gabe, you realise you’re not here permanently, right?”

Gabriel levels him a look. “With the way things are going with your _galaxy brain_ , I might as well make myself at home.”

**Tuesday,** **9:41** **PM  
** **36 hours**

“This place suits you,” Anael says as she walks into the chapel, looking around. It seems pretty shabby, honestly. Definitely wasn’t used for any actual worshipping.

Cas turns away from the altar to give her a smile. “Hello, Anael.”

“I’d hug you but there are cameras watching,” Anael says, though she tries to convey her gladness to see him in her smile. It’s no secret that Angeles is what makes Kansas work, what kept him grounded. Now that Cas is here, Anael had a little bit of hope that they’ll actually pull this off. “When I heard about the new chaplain, I just had to come down here. Did you get any visitors yet?”

“Just one inmate from A block,” Cas answers. “Does Dean know I’m here?”

“I’ll let him know tomorrow. It’s lights out in a bit,” Anael says, taking a seat on the front row of the benches. “He had this reunion with his dad today, I saw it from the surveillance room.”

Cas’s eyebrows rise a bit in surprise. “How did that go?”

“No audio input in the footage so I can’t say much. They played blackjack, I think, then he left after a bit,” Anael fills him in. After a moment, she says, “Please tell me at least _you_ have a plan.”

“I’m thinking about using an ambulance to get out,” Cas says. “Dean, Gabriel or Crowley can fake a medical emergency with Adam’s help, something bad enough that we’ll need an ambulance to come to bring them to the nearest hospital, and then Meg and Jo can hijack it. The only problem is, that’ll only work if we were getting just one person out.”

Anael frowns. It was the best plan they had when compared the crappy ones Dean and Meg had come up with and it’d immediately gone down the drain. “Well, is there a way where more than one person could go? Food poisoning?”

“Then everyone should have it, not just those three,” Cas points out.

“So basically, we have no plan again,” Anael says flatly.

“Another one I had was that we do a hostage situation but it draws too much attention,” Cas says, thinking out loud. “Or we could… never mind. Bad plan.”

“I’m desperate. Just tell me any plan you have,” Anael pleads.

Cas sighs. “Riot.”

Anael inhales sharply. “Yeah, _bad_ plan.”

“Dean’s trying to put on a brave front, isn’t he?” Cas asks.

“Like you have no idea,” Anael mutters. “We all know he doesn’t know what to do, not until Crowley gets out of the SHU tomorrow. Honestly, I think he’s scared that he’ll get caught. He didn’t have a lot of time to prepare for this mission. The first time, he had 10 years. Second, almost two if we include Bela and Crowley’s prior planning. Now, he didn’t even have a _week_.”

“Dean will get us out of here no matter what,” Cas asserts. “We could always trust him on that.”

“Can we really?” Anael asks, laughing pathetically. “You’re literally standing right there.”

Cas goes quiet.


	3. Day 3: Sins and Confusions

**Notes for the Chapter:**

> TW/ Brief mention of drugs after the flashback and talk about drugs in the last sections, plus a reference to drug use in the part with Alastair  
> TW/ Fight and death threat at the last part in the laundry room

**7 years ago**

The faint melody of _Bella Ciao_ plays over the old radio and Anael breathes in deep, taking in the moment. Though the heist on the Bank of America isn’t for another few months, she knew moments like these wouldn’t last long. Since walking into this house and seeing all the people Kansas had selected for the mission — a masterful jewel enthusiast plagued with kleptomania, a bitterly sarcastic robber wanted in the UK, a British con-woman with a flair for the grand, an experienced armed thief with the personality of a ticking time bomb, two who were a miner and a robber respectively who simply wanted to go home, a hacker who is definitely too young to be there and a shoplifter who carries a box of expired bandaids around — she knew something would go wrong.

This may be the last shreds of peace she will know in her life until she enters the bank. Once you participate in a heist of that scale, there is no going back. These people, no matter how ill-fitting, have no choice but to become family now. If one fell, the rest would in due time.

“What are you thinking about?” London asks, smiling at her through her vanity’s reflection as she tries on golden hoop earrings that Meg had gotten for her while scoping the bank. Anael thought that the two had an unspoken thing going on, though she can never testify if they’d done anything about it or simply lived in the silence just as Kansas and Angeles did.

“Just enjoying this,” Anael replies. “You know nothing will be the same once we go in?”

“Of course,” London says, turning around and leaning against the vanity to look at Anael. “Are you getting cold feet now?”

Anael huffs a half-hearted laugh, staring up at the ceiling. A thin crack runs through the painted concrete that disappears near the edge of the wall. “No.” However, she does sit up to regard London. “Have you ever gone to prison?”

London raises an eyebrow at the sudden question but humours her, “No. I never got caught. Why, have you?”

“No,” Anael echoes. “Just thinking about if we got caught this time.”

London sits down on the bed next to Anael and gives her a genuine smile — she is exquisitely beautiful and perhaps, in another life, Anael would have liked her the way Meg does. She tries to commit London’s face to memory, just like she’s been doing with everyone else. The straight line of Angeles’s nose, the sharp edges of Kansas’s jaw. The darkness in Berlin’s voice, the youth in Salem’s. The turmoil of Dallas’s hands and the brutality of Meg’s mouth. The way Rome’s words are light-hearted and Windom bears a heavy heart. Now, the beautiful fragility of London’s smile.

“Even if we get caught, our souls can still run free,” London says, bordering on philosophical.

Joking, Anael says, “I’d think that’s something Angeles would say.”

“Well, I’m the one who never got caught. He spent three years in jail,” London points out and Anael laughs.

“That is true. You’re a free woman.”

“I will always be a free woman,” London says. “They’ll never get me alive.”

**Wednesday, 8:56 AM  
** **47 hours**

_Finally, some fresh fucking air._

Lilith, the CO that drives the inmates into the prison, turns back in her seat to tell him to get out. Crowley steps out of the bus and breathes in deep, taking it all in. Spending the last two weeks in solitary was horrible. He’d been pissed to find out John got out a day earlier than he did but when he remembers that he’s going to die in twelve days, one day really doesn’t seem like such a big deal anymore.

Plus, Crowley was the one who started the fight, after all. One day extra seems like a reasonable consequence. Dean owed him one for this.

“How was solitary?” Benjamin asks. It seems like he asks this to every inmate that returns from the SHU for the sole reason of provoking them. He’s had the pleasure of sending some inmates back who tried to punch him for asking the condescending question. Crowley won’t fall for that.

“Splendid,” he says, flashing a clearly fake smile. Benjamin shoves him forward, saying ‘Gate 1-1’ into his radio. The gate slides open and Crowley follows Benjamin through.

The prison is just as busy as when Crowley left two weeks ago. From the corner of his eye, he could see Alastair slipping a bag of heroin to that kid that was in for grand theft auto. Crowley, while he did dabble a bit in narcotics outside of prison, would never deal within one. It’s too dangerous — everyone in here is too desperate to get their hands on even a pinprick of white powder. There’s always the possibility that they have no idea how much their body can take at one go.

Long story short, Crowley has no respect for Alastair. Only the pathetic sell in a prison, especially to those who have no idea what the fuck they’re doing.

“You’re back to your cell in C block. 270, you already know,” Benjamin says. He regards his radio as he says, “270, you already know. CO Jo, you take him.”

Crowley raises an eyebrow. _CO Jo?_

A CO Crowley hadn’t seen before he got sent to the SHU walks to him, her unforgettable red hair pinned into a loose bun. Though her face is trained into one of no expression, her eyes told it all — she was happy to see him.

He wouldn’t admit it, but Crowley is happy to see Anael too.

She goes behind him to direct him to his cell and once Benjamin is out of earshot, Crowley asks, “Career change, Anael? The uniform does suit you.”

The go up the stairs and fall silent as an inmate walks down past them. Once he’s gone, she says, “Me, Dean, Gabriel, Michael, Adam and Cas are here. Your mother asked for our help to get you off of death row. We couldn’t say no.”

“Hold on,” Crowley says and they remain quiet until they reach his cell. His cellmate, Ishim, thankfully isn’t there so they can have some privacy. Anael makes sure there’s nobody close enough to hear them and Crowley asks, “Where’s everyone?”

“Michael and I are COs, Cas is the chaplain, Adam’s a nurse. Dean and Gabriel are in cell 275,” Anael answers.

Crowley frowns. “But why so many?”

“Well, originally, it was just Dean, Michael, Gabriel and me, then Cas and Adam got overprotective. You know how they can be,” Anael says, rolling her eyes. “But I think Michael had a bad time in prison so Adam wanted to look out for him, and you know Dean’s never been in here before. Cas worries.”

“Sounds like them,” Crowley scoffs. Typical of them to be protective but he supposes he can see why. “Does Dean have a plan?”

Anael leans against the wall and smiles wryly. “I think he’s just as lost as the rest of us. Maybe you know something about this prison that can get the ideas going.”

Crowley considers it. “The only ways a vehicle gets in and out of prison is during visitation, medical emergencies, inmate transportation and suppliers for the cafeteria and pharmacy.”

She presses her lips together, thinking, then she says, “You should talk to Dean, maybe you two can get an idea running. You know which cell he’s in. Oh, and his name in here is his Italian one, Dino De Luca. He’s staying under the radar.”

Crowley nods and right before Anael turns to leave, he quickly says, “Even if this doesn’t work and I die in twelve days… thank you for trying to save me.”

Anael just smiles, but this time, it’s sad.

When Dean finds out which cell Crowley is held in, he thanks his lucky stars that death row inmates aren’t kept in a separate block. The last thing they all need is to get into a block full of people who have nothing to lose.

With Crowley’s return brings a new problem, though. As it turns out, someone else has been waiting for his release from solitary as well — Naomi. She had the intention to interrogate Crowley about the two heists which makes this even harder because seven of the Dalís are in the same facility. Maybe if this was happening three years ago, Dean could confidently say Crowley wouldn’t sell them out, but that’s different. Three years ago, Crowley wasn’t going to die.

He knew he had to get to Crowley before Naomi arrives to question him. According to Michael, Naomi would be arriving at 3 in the afternoon which gives Dean more than enough time to talk to him and figure out what Crowley plans to tell her. As long as John doesn’t ruin anything before 3 — today was the deadline for his answer of if he will bring John along on the break-out.

Dean’s answer hasn’t changed — it’s still a fat no.

That day, Anael had helped ensure that they were both assigned to the same duty so they would have a chance to talk. That morning, she’d secured them the task of mopping the hallways outside the recreation rooms. Crowley arrives five minutes after Dean does, wheeling the yellow mop bucket down towards him.

With a smile, Dean says, “Good to see you, man.”

Crowley pats his shoulder once — he’d never been the type to be verbally sentimental, so the gesture said everything his mouth didn’t. Dean got every word. “Hello, De Luca.”

Turning so there is no camera that can pick up what his lips are saying, Dean starts talking, “Gabriel said you’re getting interrogated by Naomi.”

Crowley nods, wringing his mop free of excess water and then slapping it down on the tiled floor. “I am. She’s coming later. Don’t worry, I doubt she would want a tour of the prison. She should only be bothering with me in one of the rooms here.”

Dean asks, sliding his mop across the floor, “What are you going to say?”

Crowley pauses like he’s considering lying, quiet for one second too long, and that second makes Dean’s chest cave in. He asks, “What would you like me to say?”

Dean stops mopping. “Crowley, are you going to sell us out?”

Sighing, Crowley continues mopping to act for the surveillance cameras, but he talks as he does the task. “What were you expecting? When you’re going to get your brain fried in two weeks, it really puts things in perspective. I have a mother to protect.”

Dean pulls Crowley to the side, out of the camera’s range, and starts, “Do you think you’re the only one with a family to look out for? Everyone sacrificed something to come here and save you, you’re just gonna throw them into the meat grinder?”

Crowley glances away for a second, trying to find the right words to help Dean see his point. His face suddenly twists into something less sympathetic, something colder, and he says, “I didn’t ask you to come and save me.”

Dean realises it then. “You were gonna sell us out anyway.”

“To buy my ass enough time to go back into hiding,” Crowley confirms. “I would have told you so you’d have time to run too.”

“I don’t give a shit about that, you were gonna give our names? After everything that we went through?” Dean asks with disbelief of Crowley’s easiness in letting all their history go for himself. It’s not like Dean wanted to fucking walk right into a jail cell, and he’s sure Cas, Gabriel and Michael weren’t excited about returning either. Anael sure as hell would prefer to not enter prison at all and Dean didn’t even want Adam here. Yet, they were all here to save him for impending death but Crowley didn’t care.

Crowley leans in close, glowering. “Yes.”

“I’m sorry,” Dean says before he slams Crowley against the wall. “You’re my friend, but I can’t let you do that.”

Challenging, Crowley grins confidently. “Have you ever killed anyone before?”

Despite the situation, the corner of Dean’s mouth lifts in a bitter half-smile as he asks, “Would you like to be the first? No electric chair, no last meal. Just you and me. You may have killed before, but I hit like a mother-fucker. I’ll make you wish you were dead if you say even one name.”

That does get Crowley thinking — nobody wants to get treated like a punching bag forever and they all know Dean could keep going if he wanted. Finally, Crowley asks, “Do you think you can run forever? Naomi will be in the prison, albeit in just one room, but there’s seven of us in here and she knows three of our faces. It won’t take long for her to connect the pieces.”

“Then we get rid of her.”

“They’ll just send someone else in her place,” Crowley points out. “We’ll be caught even quicker.”

“ _Fuck!_ ” Dean curses loudly, kicking the wall in frustration before turning abruptly back to Crowley, grabbing his collar and pulling him close, their faces inches apart. Dangerously, Dean warns, “MacLeod, I’ll only tell you this _once_. I have too much to lose now — all of us have too much to give up just because you want a ‘get out of jail free’ card and drink whiskey until you blackout.” Crowley holds his breath, eyes darting over Dean’s face, and Dean continues, “If I find out you gave up someone’s name that wasn’t known before—if I find out you gave up any of my family’s names, and I _will_ find out, no prison in this world will be safe enough for you.”

Dean releases Crowley, the slam of his body loud in the confined space, and then he grabs his mop and walks away.

**Wednesday, 12:05 PM  
** **50 hours**

“Hey, Churchy.”

Cas turns around and breaks into a smile once he realises who it is. “Dean.”

“You look good,” Dean grins, already feeling so much more at ease now that he’s seeing Cas. A part of him was concerned but his happiness in seeing Cas outweighed his being upset about it. “When I heard you were here… not gonna lie, I was unsure about it but I am so glad to see you.”

“I want to kiss you but there are cameras,” Cas says, though the way he’s looking at Dean is enough to cheer him up from the earlier argument with Crowley. “Have you thought of something?”

Dean sits at the bench and intertwines his fingers together in faux prayer, saying, “A lot of things are going wrong.”

Cas sits a row in front of him, opening the bible to pretend to read, and says, “Tell me.”

So Dean does. He tells Cas about John, Lilith and Michael, Crowley and Naomi. He tells him about his and Meg’s failures to come up with a better plan while taking into consideration everyone’s problems. He tells him about the five favours he has with Warden Roman and how he has only three of them left. He tells Cas about his concerns about his and Adam’s being here and his guilt about bringing Michael and Gabriel back to prison. He tells him about his and Anael’s disagreements on their first day there.

By the time he runs out of things to say, he realises that he is in a prison of his own mistakes now.

Cas is silent as he thinks over everything Dean relayed to him, finding solutions to problems Dean brings him like his second-in-command. For a moment, Dean lets himself pretend that they’re in the Bank of America, and they were still only Kansas and Angeles. When nobody was dead and no mistakes were made. He thinks about a universe where he never planned the heist.

Finally, Cas says, “Maybe we don’t need a plan.”

“What do you mean?”

“Despite how well you planned contingencies for the first two missions, I really don’t think you can plan for anything in here. There is no protocol to follow for criminals, you and I both know that. When have we ever played by the rules?” Cas prods — Dean knows he’s right. It’s why he and Meg didn’t plan out anything too solid, leaving enough room for last-minute adaptations. Yet, he had wished, however out-of-reach, that criminals had a code that Dean could plot around. “You’ve always been the plan, Dean.”

Dean wouldn’t go so far as to agree, though he had been the one to plan everything each time. In this situation, Dean most definitely isn’t the plan anymore. “Not this time.”

“The thing about plans is you can make as many as you want, but the truth is that life is unpredictable,” Cas says. “You make a plan, you expect it to fail, and then you throw it away. That’s how it is. We’ll have to make it up as we go.”

Dean’s hands itch to reach out to Cas, pull him close and kiss him, but with the cameras watching, it’s simply not possible without losing their cover to Naomi. He stays where he is, one row behind Cas, and settles for resting a hand on his shoulder. “What would I do without you?”

“Crash and burn,” Cas says, and though Dean can’t see his face, he knows that he’s smiling.

**Wednesday, 5:23 PM  
** **55 hours**

With his shift in the surveillance bubble wrapping up at 5 in the evening, Michael had gone to get his dinner from the cafeteria — the kitchen was run by cooking-proficient inmates, a way for them to earn 12 cents an hour which Michael thinks is way too little when they’re feeding the prison and making special meals for the guards.

He gets his set from the inmate, a young blond named Alfie that Gabriel told him about, and makes his way to the medical bay to have his dinner with Adam and Rufus. Rufus is a little rough around the edges — Apparently, he’s not so friendly with guards because some mistreat inmates for no reason, but Michael thinks Rufus is warming up to him with Adam there.

He walks through the halls, mostly ignoring the inmates. Given that he’ll only be there for less than 14 days, Michael doesn’t care enough to bother scrutinising them. They’re not his problem, someone else can do it.

When he turns a corner, he narrowly dodges someone and when he processes who it is, he freezes.

Lilith’s face splits into a wicked smile as she grabs his arm — while her hair has gotten straighter and her face is sharper, her smile is still the same amount of unsettling. “I kept wondering who CO Milligan is.”

“Lilith,” Michael says, wrenching himself free of her grip. He lies, “I didn’t know you were here.”

“Yeah, well, after the military, I figured I should get an easy work kind of job. Sit around, yell at people to listen to you, beat people when they don’t,” Lilith says casually, stepping back to leave ample space between herself and Michael. “And I thought: Hey, a correctional officer. Seemed to be a good call.” Michael nods once, dreading having to talk to her, and she says, “It’s good to see you again, brother. What have you been up to?”

Michael can’t figure out what Lilith is trying to do, why she’s being so civil with him. He still remembers the night he’d crawled out of his bedroom window and sprained his arm when he fell off. He’d been desperate enough to get away that he ignored the pain. His life of crime that came from that night, no matter what paths it led Michael down to, he still preferred it to this. Somehow, Lilith being a rational human being was even worse than when she was being insane.

He says vaguely, “Life.”

Lilith nods like he said something interesting and asks, “Hm, I was thinking more along the lines of CO _Milligan_. Now, why’d you pick that name and who is Nurse Milligan?”

“I just picked a random name. It’s a coincidence that a nurse with the same name got hired,” Michael answers.

“Then why are you bringing your dinner to the med bay?” Lilith digs.

“Rufus is good company,” Michael says tightly, his eyes draining themselves of any emotion. Lilith was good at reading fear.

She grins as if Michael has told her a hilarious joke and playfully punches his arm. Lilith leans in like she’s going to share a secret and says, “You can lie to everyone but not to me. I think I know my brother well enough. Nurse Milligan’s your husband, isn’t he?” For a moment, Michael’s heart stops at the thought that she’s going to threaten to kill Adam.

Instead, she surprises him. “And you’re cheating on him with that inmate.”

 _What?_ Michael blinks but refuses to show his confusion on his face. “I don’t know what you’re talking about.”

“I see how you and De Luca keep hiding off-camera, I know the two of you keep talking and meeting in private. I do spend time in surveillance, you know. I may not have seen your face but I can surely use the process of elimination to know which guard is CO Milligan,” Lilith says. “Don’t worry, your secret’s safe with me. You and De Luca can keep going if you’d like.”

Michael can’t believe it — Lilith genuinely thinks he’s cheating on Adam with Dean (or Dino De Luca, to her). It couldn’t be further from the truth. He barely trusted Dean with anything, let alone enough for the secret relationship she thinks they have. Though, it does mean that she likely won’t bother Adam so Michael will roll with it. At least he can try to look out for Dean. Keeping track of Adam in the medical bay from the common areas is much harder.

“You’d get fired and probably sued if you get found out, though,” Lilith says. “Last year, there was this CO who—”

“I really don’t need the details,” Michael interrupts.

She laughs, sharp and nails on a chalkboard to Michael, and says, “You’re a riot, Michael. Well, I won’t keep you. Go and eat with _your husband._ ” With that, Lilith whistles to herself as she leaves into the other hallway and Michael lets out a breath.

He hadn’t expected this, they’d gone through a whole conversation without her trying to kill him or bringing up her “holy mission”. It went a lot better than Michael thought it would have, but it doesn’t mean he’s going to let down his guard.

Dean has been watching and memorising as much as he can about the prison for the past three days.

They all get up at 8 to wash up so the bathrooms are full of almost every inmate at the time. Breakfast lasts until 9:30, then they have their work assignments (in which Dean has deigned to work in electrical while Gabriel scores the place in commissary after the previous inmate got sent to the SHU for smuggling contraband). At 1, they have lunch and then it’s free for all until dinner at 5. Curfew is at 11, though numerous inmates seem to continue sneaking around after the lights turn off.

Electrical doesn’t have many inmates there — Dean assumes that it’s because it’s one of the lower-paying jobs in the prison compared to other ones like the kitchen. It’s about half the wage but Dean doesn’t mind, it’s not like he’s going to be there forever. Michael and Anael can get him anything, he doesn’t need the commissary money.

He also keeps track of the more notable inmates — Alastair White who apparently deals drugs to other inmates and uses a CO to bring the supply in. Dean thinks he’s working with Lilith, though he can’t be too sure. Ishim doesn’t have much of a reputation in the prison; Dean’s only concern with him is that Ishim doesn’t seem to take a liking to Gabriel and he’s obviously a violent inmate. There is also Asmodeus Prince, another contraband smuggler other than the previous commissary guy. He keeps his head down so probably not much of a concerning figure.

As for COs, there’s Benjamin who regularly provokes the inmates. There’s Lilith, Michael’s sister and likely working with Alastair. Head Guard Bartholomew, though Dean doesn’t cross paths with him often. Of course, Warden Dick Roman who is no threat to Dean at all.

With everything he’d learned, Dean knows one thing — to get out, they’ll need to pick a place the guards rarely patrol around. They tend to stick to the common areas more so Dean has spent his time exploring the non-restricted areas to find spots to start plotting an escape from. So far, he has the back area of the yard, the laundry room and the kitchen. The yard seems like the best option — closer to the road.

For now, though, Dean heads to dinner. Michael’s apparently been spending his evenings at the medical bay with Adam and Anael takes her dinner to the surveillance bubble to eat with Hannah. Cas tends to stay in the chapel because he doesn’t want to remember the worse parts of prison. Gabriel and Dean sit with Alfie who’s actually a good kid. In the back of Dean’s mind, he thinks Alfie would have made a nice addition to their family.

Tonight, John Winchester settles across the table from Dean.

“I want my answer,” John says, stabbing undercooked meat with a plastic spoon.

“It’s still a no,” Dean replies, folding his arms on the table as he gives John a pointed glare. “What the hell were you expecting? For me to say yes? Because I really don’t know what makes you think I’d get you out of here. I don’t owe you anything.”

Some time while Dean is talking, Alfie seems to have slipped away to a different table, not wanting to get involved. Smart. Gabriel simply stays put next to Dean, though he continues eating like the conversation isn’t happening.

“You do remember what I said before?” John asks.

Dean considers it. “Meet me in the laundry room at 12:15.”

John lifts his tray without another word, only regarding Dean with a challenging stare, and walks off to another table.

Gabriel watches him go with curiosity in his face. “What the hell was that?”

“He’s going to tell a CO that we’re planning a breakout,” Dean answers, his eyes following John to make sure he doesn’t talk to any COs. “We’re gonna have to handle him.”

Gabriel leans closer to him. “Handle him as in?”

“Beat the shit out of him before he tells a CO,” Dean answers. “Or we kill him.”

**Wednesday, 11:57 PM  
** **61 hours**

Adam had given him a chaste kiss at the doorway of the medical bay when Michael passes by on his night patrol. While Michael is constantly worried about the inmates that filter through the med bay and put in a room with his unarmed husband, Adam seems to be handling himself fine. In fact, Michael thinks some of the inmates actually like Adam’s kindness, especially when dealing with the cruelty of the correctional officers in the common areas.

The good thing about Adam being there is that Michael gets to enjoy the little things. If anything happened, at least he has these moments.

“I’ll see you tomorrow,” Adam mumbles against his lips. Michael kisses his cheek and tells him good night. With Michael having a night shift for patrols and Adam wanting to stay to help inmates with late-night injuries, neither of them really leave the prison for very long. It’s almost suffocating for Michael, feeling like he’s trapped again, but he tries not to let it be known to Adam.

He leaves for the cells, walking past and checking if inmates are where they are. If some of them are missing, he doesn’t bother reporting it. Again, not his business. He’s not planning on getting shanked by a provoked inmate.

He passes by cell 275 — Dean isn’t there, though Gabriel is sleeping soundly. Michael keeps on walking. Surely, if Dean needs his help, he’ll ask for it.

When he passes 302, he gets yanked into the cell and pushed up on the wall by two inmates that are collectively stronger than he is. It happens too fast for Michael to react and he barely processes who is standing in front of him — Alastair.

“What the hell do you want?” Michael asks, deciding that there’s no harm in finding out what he wants from him on the off-chance it’s something that can help with the plan’s development.

“I have a business proposal for you,” Alastair says. His voice is like an embodiment of a snake, and it sends chills down Michael’s spine. “I need you to bring something in for me.”

“No,” Michael instantly says. He knows what Alastair does within the confines of the prison walls. He doesn’t want the trouble. “I don’t do that.”

“Come on, now. Don’t lie. I see all sorts around here,” Alastair says, rummaging through his belongings to find what he’s looking for. Michael watches him, ready to protect himself if necessary, and Alastair continues speaking, “Kids who are new to it, people who’ve been doing it for years, people who jump right back in after years of skipping out. I’ve seen it all and I know someone’s done it before when I see it.”

He turns back, holding up a small baggie with white powder that’s all too familiar.

Michael draws in a deep breath. “I got clean years ago.”

“But you miss it, don’t you?” Alastair asks, bringing the baggie closer to Michael and waving it like it’s a bait and Michael’s a river full of hungry fish. “Look at you, your hands are shaking.”

Michael feels betrayed by his body, and he curls his hands into fists. “You’re fucked up, you know that?”

“This is a prison, everyone here is fucked up.” Alastair laughs — it sounds like nails on a chalkboard, so unpleasant that it leaves something dreadful in the cavity of Michael’s chest. “I have a proposition. CO Monroe keeps asking for a bigger cut and I’m not paying her any more than I already am. 50% is a ridiculous demand, don’t you agree?” He doesn’t wait for Michael’s response and gets right up in his personal space, the baggie even closer to his face now. Michael turns his face away, trying to lean as far back as he can while being cornered to the wall. “I extend the position to you instead. Someone who already knows how this works. I’ll give you 30%.”

Michael frowns. “No.”

“No?” Alastair echoes, a slimy smile crawling onto his face. Michael has met a lot of people in his life, but damn him if Alastair isn’t one of the creepiest. Alastair slips the baggie into the breast pocket of Michael’s uniform. “Take this as an incentive. A welcoming gift. If you don’t do this, I know coincidences never happen and that new blond nurse and you are a _very_ big Milligan coincidence.”

Michael’s aware of his implications and he despises the way he doesn’t say anything in response. It’s not that he’s scared of Alastair — rare, it was, for anything or anyone to truly scare Michael, and he knows that Adam can take care of himself — but rather that he was scared of what lays in the baggie in his pocket.

Forcing his voice into one that’s firm, Michael straightens up and says, “Go to bed, inmate.”

Alastair grins and nods to the side, and the other two inmates leave Michael’s side to return to their cells. Alastair lingers, pats Michael’s chest over his heart where the baggie now is, gives him that disgusting smile and then walks away into the dimly lit halls of the prison.

Suddenly, Michael can’t breathe, and he ducks into the nearest empty room — a small recreational room for inmates studying for a GED that’s only used in the afternoon. The tables are already stacked at the side, leaving bare tiled floor.

He slides down the wall and drags in a breath, trying to forget about the baggie in his pocket and where he is.

“What did you work as before this?”

Anael glances over at Hannah — they’re not the most intimidating looking person which confuses Anael a little bit. The idea that Hannah has served in the military is almost unbelievable with how small they seem. With gentle brown hair that reaches their shoulders and blue eyes so pale and crystal, they seemed more like they’d go for an office job than working among criminals.

“I worked with money,” Anael answers. It’s not like it’s a lie, she did work with money. Though, while Hannah would be thinking accountant, Anael is talking about conning people of their money.

“My brother’s an accountant. It makes him really particular about money. He absolutely loses it when I spend too much at one go,” Hannah says lightly and conversationally. It’s clear that the two don’t have much in common, but bless Hannah’s soul for trying to keep Anael entertained while they work the surveillance shift.

Looking over the monitors, Anael leans closer to the screens when she sees who looks like Alastair pulling Michael into his cell. “Did you see that?”

Hannah turns their attention from Anael to the screen, missing the scene by barely a second. “No, what?”

Anael doesn’t answer, squinting as she tries to make out what little of the cell she can see from the camera’s grainy image. She can see Michael pressed against the wall and Alastair saying things, the words lost to the lack of audio input and distance. At some point, he slips something into Michael’s pocket, and then he pats his chest twice before Michael stumbles out, looking disoriented.

This time, Hannah does see it. “What’s wrong with him?”

“I don’t know, I’m going to check it out. You okay with handling Alastair?” Anael asks.

Hannah says, “Someone has to stay here and look at the cameras. I’ll send Uriel, looks like he’s coming by to his cell soon anyway.” Anael nods, not exactly concerned with how they plan to deal with it, and leaves without another word. It seems like he’s heading towards the rec rooms so she follows the signboards to get there.

There, she looks in the windows of every room until she finally sees Michael in room 3. Quietly, Anael opens the door. “Michael? What did Alastair say?”

She moves closer and Michael wordlessly pulls out a baggie from his pocket. Anael takes it from him, turning away from him to open it and get a better look at the contents. From the smell of it, it’s heroin. She sharply turns back to him, glaring. “You’re buying from Alastair? Michael, you cannot be serious, we’re trying to break Crowley out—”

“I’m not buying it!” Michael cuts over impatiently. “He’s trying to make me smuggle his supply into the prison instead of Lilith.”

Anael pauses. “Why you?”

“Because he could tell that I—” Michael stops himself. Anael notices then, the way his fingers are fidgeting. She’s seen it before with Ruby and instantly feels guilty of her accusation. “Can you get rid of that?”

Anael slips it into her pants pocket, nodding. “Yeah, I’ll take care of it. I’m sorry for jumping to conclusions.”

“You didn’t know,” Michael replies, staring at his shoes. Anael sits down by his side.

“So that’s why Adam got all scared?” She asks. Michael nods wordlessly — there’s no need for any more elaboration or explanation. It’s obvious Gabriel also came because of this problem. Since Gabriel and Michael were in prison together as cellmates, it makes sense that Gabriel would be concerned enough to join the break-out mission. “Does Dean know?”

“No, and he doesn’t have to,” Michael says firmly. “Look, he’s got enough to deal with. The whole Alastair and Lilith thing, I’ll deal with it on my own.” Anael begins to protest but Michael insists, “I don’t need his help. He just needs to focus on getting Crowley and Gabriel out and his father. The rest is our problem.”

Anael tucks the baggie into the pocket of her pants, wondering if she should file a report against Alastair or simply dump it in a toilet bowl and forget about it. Granted, the prison is not her concern, but she cannot have Michael getting tempted by a ready supply. Plan or no plan, it’s not good.

She almost makes it back to the surveillance bubble before Dean catches her in the hallway. “Have you seen Michael? I’ve been looking all over, can’t find him.”

She hesitates — Michael had been in the middle of panicking earlier and so she wasn’t sure if he can be of any good help to Dean. She asks, “Why?”

“I need to take my dad out of the equation while still saving my favours,” Dean explains. “He’s a little stronger than I am, I’ll need to make it quick because Bartholomew’s doing rounds tonight and he’s thorough. Where is he?”

Concerned, Anael offers, “I’ll keep watch, make sure Bartholomew doesn’t see you.” Dean doesn’t protest, taking up her help, and they move to the laundry room. Michael remains silent the whole time, his jaw tight, and before long, they’re there.

Anael leaves them at the entrance to serve as a sentinel for them while they deal with John and Michael and Dean go into the area the cameras don’t cover. It’s a wonder that Warden Roman hasn’t done anything about the blind spots, thought Dean’s pretty sure that Roman doesn’t give a fuck.

John turns to them and raises an eyebrow. “Why’s your friend here?”

“Sorry. Can’t let you come along, but can’t let you talk either,” Dean says before his fist collides with John’s jaw. John stumbles back, not foreseeing the attack, and then Michael grabs a fistful of John’s collar, slamming him against the wall and punching him twice. Though he had no personal business with John Winchester, he needed the release and what better outlet than Adam and Dean’s shitty father?

He steps back enough for Dean to take over, shoving John to the ground to kick him. John rolls out of the way in time and grabs Dean’s foot, pulling him to the floor with him. He scores a hit to Dean’s cheek and then Michael picks up a metal tray and whacks the side of John’s head with the edges of it from behind.

“Dean,” John mutters, out of breath. “Stop.”

“This is about more than you talking,” Dean says, making sure John stays down. His face is clearly hurt, his nose leaking crimson, and his uniform has been dirtied by their shoes. “This is about how you left me and Sam! How you left Adam and his mom! All the bullshit you said to us, and the bullshit you never did. How you never left Sam and Jess alone no matter how many times they asked. You just never know when to stop.”

“I didn’t even know about Adam until he was 10—”

“That’s not an excuse,” Michael interrupts, his voice dark. “You will not say anything about the plan, because there isn’t one. Do you understand me? We’re giving you two choices. One, you walk out of here and tomorrow, you leave Dean alone. Two, you die in a laundry room.”

Dean adds, “And don’t bother telling any COs. They’ll believe Michael over you any day.”

John reluctantly relents, knowing that he’s severely outmatched with two experienced fighters. Dean knows John’s a stupid guy, but not stupid enough to not know that he’s out of his depth. Dean knows that he’s clearly good at fighting, and with that cold stare in Michael’s eyes, Dean’s sure that John is intuitive enough to guess that it’s not Michael’s first time handling murder.

“Fine,” John gives up.

Michael says, “If I find out that you reported Dean or Adam, or any of us, to Bartholomew or Roman, I won’t be so kind.”

Knowing when he’s beaten, John raises his hands in surrender, and Dean drops John to the floor to recollect himself. He turns to Michael and nods towards the door, regrouping with Anael. She uncrosses her arms when she sees them coming her way and asks, “How did that go?”

“He said he won’t say anything,” Dean assures before he turns to Michael. “Dude, you were like Terminator or something. Are you okay?”

“Fine,” Michael says firmly. “I’ll see you tomorrow.”

He leaves without saying anything else — Anael thinks he’s going back to the med bay to relay what happened to Adam — and Dean refers the question to her instead, “Do you know if anything’s going on with him? I have to know everything, Ana.”

She contemplates telling Dean about Alastair’s proposition and Michael’s history. Though the more she thought about it, the more she remembered that Michael didn’t want Dean to know and it wasn’t her business to tell. So, Anael lies, “Everything’s alright.”

**Notes for the Chapter:**

> (If it seems like Cas and Adam don't have a very central role, it's because they don't. They already said they're only there to keep an eye on their partners and that they will stay out of their way as they find a way out of prison.)


	4. Day 4: Everything Is Fine

**Notes for the Chapter:**

> TW / Drug aftereffects in 9 years ago section  
> CW / Mention of a weapon after 7:24 AM section  
> TW / Mention of death at 11:36 AM section  
> TW / Violence (fighting, slight suffocation, graphic stabbing, blood) at 3:43 PM section  
> TW / Near-death, blood after 3:43 PM section  
> CW / Mention of drugs at 9:52 PM section  
> CW / Referenced past drug overdose after 9:52 PM section
> 
> It's kind of a heavy chapter so if you can't read it, I put a summary in the end notes.

**9 years ago**

Gabriel walks into the empty bathroom, wincing at the faint stench of heroin. He hates the vinegar-like smell but he follows it anyway to the last stall in the shower and pushes the curtain away. Michael is there, sitting on the floor as he leans against the wall, with his eyes shut and lips parted in ephemeral euphoria. Between his fingers is a cigarette — from the look of it, it’d burnt out a while ago — and a slight tremble that makes Gabriel feel sick.

“Michael, what the hell did you do?”

Michael slowly opens his eyes and pulls his gaze up from the dirty floor tiles to Gabriel, scoffing quietly once he processes who it is. “I just wanted to be numb for a bit, okay? Relax.”

“Relax? You’ve gotta be kidding me.” Gabriel pulls the curtain shut behind him to give them some semblance of privacy and sits down next to Michael. Clearly, he’s been here for a long time, the aftereffects having kicked in by now — he’s drowsy, barely able to keep his head up, and breathing slowly. His skin still has a slight flush to it and Michael’s eyes are unfocused and hazy as he frowns over at Gabriel. Horrified but not wanting to show it, Gabriel schools his voice into something more steady as he says, “I thought you said your ex wouldn’t want you to touch that shit.”

“I said a lot of things three years ago,” Michael replies, pressing his hand to his eyes as he begins to sober up.

“Who the hell sold to you? The CO?” Gabriel asks. When Michael doesn’t answer, Gabriel shakes his head — he always hated Webb, he will sell to any vulnerable person he can find in this prison. “What did you give for that?”

Michael sighs, obviously too tired to answer all of Gabriel’s questions in his state, but answers, “All my commissary.”

Gabriel stares at him. “Dude, that’s a _lot_. Weren’t you saving it?”

Michael rolls his eyes and says, “It’s either my money or my dignity and I refuse to do _that_ for heroin.”

Huffing a disappointed laugh, Gabriel says, “Of all the things to blow your money on… _heroin_ , really? What if one day, you take too much and I’m not around to—”

“This is all I have,” Michael grumbles, holding up the spent cigarette. “I don’t have any more money and I’m not desperate enough to do sexual favours so this is my last hit for a while. Guess I’m going cold turkey.”

Thinking about it further, Gabriel asks, “What’s really bothering you, Michael?”

“I spent a month in solitary for fighting in the kitchen.”

“I know, I meant what _else_ is bothering you,” Gabriel corrects, watching the way Michael seems to be drifting in and out of sleep, ready to get him help if he needs it. “That wasn’t your first time in the SHU, even for this long, and you never came back out looking for drugs until now. What was the real problem?”

Michael straightens up at Gabriel’s concerned stare, unwilling to look any weaker than he already does. “ _Fine_. My fucking ex, okay? Leave me alone, Gabriel, shit.”

“You never told me what happened between you two,” Gabriel says. “In my experience, talking helps. You know, my little bro, Cas, he would just bottle up all his problems inside. I think he hated it if people thought he was weak. I swear, he could be dying and he’ll just get back up and back in. A little bit like you, I think.”

Michael listens as best as he can through the fog of his mind, and he mumbles, “I didn’t want him to wait for me.”

“Because you have four years.”

“Exactly,” Michael says. “And I _regret_ it. What I would give to—just the thought of being called to visitation and going into that depressing room to hear his voice through a phone and seeing his smile in a window, just to see him look at me. Press our hands up against the glass. Hear him say my name again. God, I want that so bad. I _need_ that. And I let him go like an idiot.”

Gabriel tries, “You were just being selfless, Michael. Hey, you only have a year left. Maybe less than that if you try to keep good behaviour in the next couple of months. Once you’re out, you could go look for him again.”

Michael looks over at him. His pupils are slightly less dilated now, but Gabriel can still barely see the green in them — it’s unsettling. “And do what? Do you think he hasn’t moved on yet? It would have been _four years_ , Gabriel. A lot happens then. He could be married for all I fucking know. Maybe he’s got a lucky jackass with a college degree on his arm and they have a kid that has his eyes and a place in a neighbourhood with some stupid name and they’re living happily fucking ever.”

“And what if he doesn’t?” Gabriel counters. “What if, and bear with me here, there’s a chance that even though you told him not to, he’s waiting for you anyway?”

Laughing deprecatingly, Michael says, “Nobody would wait for me, I’m not worth it. It’s a very off-chance thing that you’re talking about.”

“Then on the off-chance that the love of your life is still waiting for you, you want him to see you like _this_?” Gabriel asks. “What would he say if he knew what you were doing?”

Michael is quiet, but Gabriel can tell that he’s thinking now. Michael’s throat works as he blinks himself into a more sober state. “He’d be disappointed.”

“I can tell from what you tell me that this guy really loves you, man. So if you won’t do it for yourself, then at least do it for him,” Gabriel says.

Michael shuts his eyes and breathes in deep with all the guilt and resentment he had to offer.

**Thursday, 7:24 AM  
** **69 hours**

Dean catches Crowley in the bathroom early, before anyone else is there. It’s not hard to realise that Crowley would be there — he hated crowds and typically woke up earlier than most people. At least, he was always one of the first to get up when they studied for heists. Plus, with how dirty the bathrooms get and how long the line will go when the clock hits 8, Crowley would be a fool to not beat the queue.

When Crowley comes out of the shower cubicle, dressed, Dean’s already waiting for him.

“Morning, De Luca,” Crowley greets half-heartedly. “Did you need the shower?”

Dean gets right to it. “What did you tell Naomi?"

Crowley stops in front of the mirror at the sink to see if he looks presentable, saying, “Relax. I gave no names. Despite the odds, you have managed to get me out alive every time. I’m trusting you one last time.”

Dean exhales, relieved. “If I find out you’re lying, I swear—”

“Yes, you will beat the ever-loving fuck out of me,” Crowley mutters, rolling his eyes and turning back to look at Dean. “I am aware of your violent resolutions and contrary to popular belief, I don’t actually like it when people hit me. I heard that you and a certain John Winchester met in the laundry room. What was that about?”

“He wanted to hitch a ride,” Dean explains. “I didn’t want to let him come along.”

Crowley stares at him, looking as if he’s reluctant to ask after it. He does, hesitantly, “Did you kill him?”

“ _No_ ,” Dean quickly clarifies. “It would just be extra trouble. We beat him up and left him there. That’s it. We left him alive.”

Crowley nods, though his lack of certainty is unsettling. “And you are sure he will no longer harass you?” Dean hums to affirm it. “Do you have a plan?”

“What’s your work assignment?”

“The kitchen,” Crowley answers. “Ironically enough, they don’t want my medical talents in the pharmacy.”

“I’m getting reassigned from electrical to the kitchen, and so’s Gabriel,” Dean says. “Dorothy’s gonna hijack a supply truck and pick us up. We’ll be out of here before lunch ends as soon as all three of us are assigned to the kitchen.”

Crowley cocks his head. “One of your last three favours? So you have two left?”

“Three,” Dean corrects. “One was to get me and Gabriel in. Two is getting us into kitchen.”

“Your big plan is just leaving through the kitchen.” Crowley looks unimpressed — for good reason, the plan is admittedly largely unimpressive compared to Dean’s grander schemes. But he had half his life for the first, a year for the second, and barely a week to pull the mission together for this prison break. This is the most stable plan Dean could find after three days.

“Yep,” Dean says.

“This is going to go very wrong,” Crowley warns.

Dean nods once, sighing. “If it goes wrong, then I’m going down swinging.”

“ _Hey, Ana._ ”

Anael smiles, pressing the phone to her ear as Hannah puts in earbuds to give her privacy. It’s the first time she and Ruby are calling each other since she entered the prison and doesn’t it feel good to hear her voice. “Hey, babe. How are you?”

“ _I miss you_ ,” Ruby answers, the quiet sound of shuffling as she makes herself comfortable on the couch. “ _How much longer are you staying in Missouri?_ ”

“I’m not sure. I think it’ll be at least another three days,” Anael estimates. Hannah goes through the mail, cutting open another envelope to read the contents. Anael thought the whole process of filtering the mail is invasive, regardless if the recipients were criminals or not. Everyone deserved some level of privacy. However, as long as she’s here, she’s going to have to drag the black marker ink across anything questionable.

Ruby sighs loudly and Anael chuckles, using the penknife to cut open another envelope. The letter is addressed to one of the younger inmates from what sounds like is a member of his gang. Anael tries not to blot out too much from the letters.

“ _I thought you Dalís made a big show of your heists_ ,” Ruby says.

Hannah holds up a letter towards Anael, an amused grin on their face, and Anael reads the line they pointed out — _Why are you looking at the monkey outside the window when I am here?_ Hannah mouths ‘what monkey?’, and Anael grins.

“That’s for _that_ , babe,” Anael says. She’s not sure how sound-proof Hannah’s earphones are but she’s not taking the risk. “This one’s different. We only have ourselves.”

“ _That’s boring._ ”

“Don’t let Dean hear you say that,” Anael jokes, looking out of the door to see Alastair walking past the office. Her eyes drop to his hands; they’re empty, but she spots it in the waistband of his uniform — a shiv. Anael taps Hannah on the shoulder, pointing to the door where Alastair has already disappeared and says into her phone, “Sorry, Ruby. I have to go. Love you.”

She doesn’t wait for Ruby to return the statement, hanging up and standing. Hannah takes out their earbuds, confused. “What?”

“Alastair has a shiv,” Anael says, quickly exiting the office to look for him. The bastard moves fast, she’ll give him that.

Hannah says into their radio, “Surveillance, do you see White?”

Uriel’s voice comes through. “ _Not that we can see._ ”

“Fuck,” Anael curses, gesturing to Hannah to split up to look for Alastair. As soon as Hannah is gone, she switches to her private channel with Michael and says, “Alastair has a shiv. I don’t know who he plans to get, but you check on Dean and Gabriel.”

“ _Okay._ _Do you need me to come with you?_ ”

“I’ll be fine, I’ll update you,” Anael replies, cutting across a hallway.

**Thursday, 11:36 AM  
** **73 hours**

John Winchester is dead.

Anael found his body in the laundry room with a shiv in his side. He’d bled out, and the crimson stains the cement floor. Clearly, Alastair’s work, and though Anael tried to get him reported and thrown to solitary confinement, Lilith had made an effort to be his alibi and purely because Lilith worked there longer, the warden believed her and let Alastair stay.

According to some inmates, John apparently owed Alastair money for cigarettes and the dealer simply got tired of waiting.

She meets with Dean and Gabriel in their cell. Once they’re sure nobody is listening, she says, “Dean, Alastair killed your father.”

Gabriel’s gaze is concerned, instantly turning to Dean, but Dean’s own gaze remains blank. Gabriel asks tentatively, “Hey, Winchester. You good?”

“I don’t know,” Dean answers. He’s not sure how to feel, because he’s feeling so much at once. A sadness that he despises born out of the obligation of family, a growing ecstasy at the idea that his nightmarish father is now dead, and a deep-seated irritation that he wasn’t the one to put John in the ground. He’s stuck between feeling happy, mournful and angry.

“Lilith wouldn’t let me send him to the SHU,” Anael informs. “The CO that Alastair’s doing business with is her.”

“I knew it,” Gabriel says, looking moderately triumphant at his correct guess.

Hesitant, Anael adds, “And Alastair’s pulled Michael into that.”

Dean snaps out of his thoughts at that. “What do you mean?”

“He wants Michael to replace Lilith to bring his stash in,” Anael explains. “Michael said no, but I don’t think Alastair’s the kind to take that for an answer. You saw what he did to your dad.”

Dean nods, trying to organise his thoughts. “Okay. Gabriel and I will join Crowley in kitchen duty, I’ll start setting up a hijack with Dorothy and Meg. John’s gone, so that’s one less thing to think about. Try to keep Alastair away from Michael, Lilith is a big enough problem for him. I’ll let Cas know about all this, someone tell Michael and Adam.”

“I’ll do it,” Gabriel volunteers.

“Alright. Then we should be out in three days, more or less,” Dean says.

**Thursday, 3:43 PM  
** **78 hours**

Michael and Adam spent their lunch break in the medical bay alone since Rufus went out for lunch with his wife Aretha. Lunch and dinner have been some of the only peaceful moments of time Michael can find, mostly because he gets to be around Adam.

During lunch, Gabriel came to them and told them the new updates — John was killed by Alastair and the new plan is to hijack a supply truck and escape from the kitchen. After Gabriel left, Adam told him he’s glad that there’s finally some semblance of a plan, but Michael isn’t so sure that things are ever that easy. Not for them, at least.

Lunch goes by too fast for Michael, and he was back on patrol around the prison. Thankfully, things usually remain quiet on his rounds. Most of his patrols were stationed in Dean, Crowley and Gabriel’s block, which Michael had discovered is apparently the most docile of the four blocks. B block holds the reputation for most violent happenings.

Alastair seems to be keeping a low profile since stabbing John to death last night. He’d walked past Michael a few times without even making eye contact. He’s certainly not going to complain about being ignored by the dealer. Adam had been concerned after finding out about what Alastair does in the prison, but Michael convinced him that he would be alright.

Michael goes because he can’t possibly say no — he’s working, after all — and as soon as he makes it to the hallway where rec room 7 is, he’s roughly dragged into rec room 5 and punched. Instincts kick in and Michael grabs the person’s arm to see who it is.

 _Lilith_. Of course. Because Michael can’t have anything good.

“What the hell are you doing?” Michael hisses. Lilith wrenches her arm out of his hand and hits him again. Michael ducks away in time and her fist misses him.

“I tried to give you the benefit of the doubt. I thought that, maybe, you’re different now, but then you work with Alastair and steal my business,” Lilith says poisonously.

Michael instantly denies, “I told him no.”

“I don’t believe you!” She shouts, lunging at him. Michael shoves her away and she continues, “God was right! You should be dead!”

Michael inhales sharply. It really was too much to ask that she had lost the delusion.

“Years and years, I tried so hard but always failed,” Lilith says. “But finally, I will fulfil God’s will.” She grins, shoving Michael against the wall. His cheek brushes the rough concrete of it and he pushes himself off, grabbing Lilith and twisting her arm behind her back to apprehend her.

“You are insane!” Michael shouts. “God isn’t talking to you!”

Angrily, Lilith raises a leg and kicks the heel into Michael’s shin. “You don’t know that!” He flinches at the pain and she takes advantage of it, turning around to slam her fist into his face twice.

Michael stumbles backwards — the military training Lilith had as opposed to whatever brute force Michael acquired over his criminal lifestyle makes up far too great a difference in the fight. Where Michael is strong, Lilith is quick, muscle memory from training kicking in. He straightens up and decides that there’s no point in trying to reason anymore so he punches her back.

A sharp laugh bursts from her and she lunges out, reaching for the radio clipped to Michael’s shoulder. Pulling at it, she grabs Michael’s arm and uses the momentum to turn him so she can wrap the wire around his neck. She tugs on the radio and the other end of the wire and Michael chokes, pulling at it to give himself leeway to breathe.

“This is what I should have done long ago but you had to run away,” Lilith says lowly in his ear.

“Because you’re crazy! You’re trying to kill me!” Michael says, strained, releasing his grip on the wire and instead, reaching for Lilith. He grabs the back of her uniform and bends, pulling her over his shoulder and slamming her onto the ground.

She groans but rolls from her back onto her knees and gets back up, trying to punch him. With the blow to her body, she’s a little disoriented which works in Michael’s favour.

Sick of the fighting, knowing that they can both go on forever, she brandishes a bloodied shiv and impales Michael in his abdomen.

Michael slows down, the pain numb with being caught off-guard. It’s clearly the same one Alastair used on John. Lilith notices his eyes fixing on the shiv and smiles, asking, “Do you like it? I stole it from Alastair.”

She pulls the shiv out and then shoves it back in, making Michael grit his teeth as he tries not to look too vulnerable. Irritated with the suppressed reaction, Lilith has always been sadistic, so she twists.

Michael can’t stop a tear from coming out, out of pure agony.

She leaves the shiv in his abdomen as she stands, watching Michael’s hands desperately try to keep pressure on the wound without bothering the blade. Before she can do anything else, Elijah’s voice comes over the radio, saying, “ _CO Monroe, there’s a fight in B block. The brothers again._ ”

“Today’s your lucky day,” she says, leaving him in the rec room as she leaves to handle the fight.

When he’s certain Lilith won’t return, Michael tries to stand — he can _feel_ the blade in there.

He stands, catching a blurry vision of his reflection in the rec room’s mirror. His blue uniform is stained a discomforting crimson, and his mind keeps going _Adam, Adam, Adam._ He needs to find the med bay.

Walking proves to be even more painful with every step and he squints to read the signage. The medical bay is too far, but the closest place he can see is the chapel, only three hallways away. Michael nods to himself, biting his lip to be quiet, and forces himself to move. He just needs to get to Castiel in the chapel and he’ll handle the rest for him.

His mouth tastes like metal.

Dean folds his arms over the top of the bench, watching Cas clean up the altar. “I keep thinking you’d look really good in a CO uniform. That blue would really make your eyes pop.”

“Dean, stop flirting, we’re in prison,” Cas says with feigned seriousness. A smile graces his face as he continues, “And I’m a chaplain. It’s inappropriate.”

“We met while you were escaping from the police with a bag full of stolen diamonds and your gun in my side,” Dean points out. “Everything about us is inappropriate.”

“Fair point.” Cas chuckles, finally turning to look at Dean. “So, kitchen duty. I’m surprised you didn’t get that in the first place. You cook very well.”

Dean nods, agreeing, but says, “I am good with classic tech too, though. Engines, all that crap. I used to work on cars, you know this already.”

Castiel waves his hand to gesture to Dean to make space. Dean shifts inwards at the bench and Cas sits by him, saying, “I’m aware of your skills. But I’d think you would have gotten the higher paying job.”

“I’m not gonna be in prison forever,” Dean says, amused. “You do remember we’re rich, right?”

Cas rolls his eyes, settling in close to Dean. “I do. Call it past experiences kicking in. This one time, there was a job assignment that paid a dollar an hour. I believe it had something to do with construction. So many inmates tried to get it, including me.”

Dean raises an eyebrow. “Did you get it?”

“No. This may come as a surprise to you, but my talents do not lie in brute force,” Cas says with his typical deadpan humour, and Dean just loses it.

“Well, their loss.”

“Their loss,” Cas agrees, huffing a soft laugh. “I worked in commissary when I was in prison. It wasn’t bad, I secretly ate snacks or snuck stuff back to my cell with me so I didn’t have to spend my own commissary money.”

Cas doesn’t talk about his prison life often, so this is as much information about it that Dean has ever heard. Dean smiles slightly., leaning closer with fondness in his eyes. “Always the kleptomaniac.”

The doors suddenly swing open and Dean and Cas automatically move away from each other, heads turning to see who it is — Michael’s clothes and hands are stained a horrifying red, a shiv sticking out of his abdomen, and he whispers, “Help.”

Cas, being the one sitting on the outside of the bench, is out of his seat first, running over and catching Michael just in time before his legs give out. He tries to hold Michael up, calling, “Michael!”

Cas, panic tight in his throat, stops thinking rationally and his brain goes: _take the blade out and see what you’re dealing with_. He grabs the shiv and pulls it out before Dean can tell him not to. Michael winces hard and collapses, bringing Cas down to the ground with him. They both fall onto their knees. Cas takes the radio off of Michael’s shoulder, going on the private channel to call Anael, and Dean kneels down in front of Michael.

To Dean and Cas’s relief, Adam had been on his way to the chapel, intending to talk to Cas, so he arrives in time. Adam falls in front of Michael, pressing his hands to Michael’s face and patting his cheek lightly. Michael’s eyes shift in and out of focus on Adam’s features. “Hey! Stay with me. You _promised_ me. _Look at me._ ”

Michael struggles to say something in reply, and his eyes slide shut.

“ _Wake up!_ ” Dean tries, shaking Michael’s shoulder.

Adam looks up at Cas, still on the radio, and asks, “Where the hell is she?”

Right then, Anael appears at the door. “I’m here, I’m—” She freezes when she sees them. “Oh, _fuck_. That’s a lot of blood.”

“I said wake the fuck up!” Dean says again, helping Adam to get Michael up off the floor.

“Get him to the med bay with me,” Adam says and Dean nods. They throw Michael’s arms over their shoulders and start moving quickly down the hallway.

Anael asks, “Who did that to him?”

“I don’t know,” Cas says, worried, holding up the shiv he pulled out. “This was in him.”

Anael takes it from him and frowns. “This is Alastair’s. But he was seen on the cameras. Someone must have stolen it.” She glances back at the bloodied floor and says to Cas, “You go help them. I’ll try and find out what happened.”

Cas runs after the three, leaving Anael with the shiv to find out who exactly stabbed Michael.

**Thursday, 9:52 PM  
** **84 hours**

With Adam and Rufus working on Michael in the medical bay, Dean can only find Gabriel and tell him. Gabriel and Michael have always been close since they met in prison, and expectedly, Gabriel gets worried. He keeps asking Dean to tell him as soon as Adam has Michael handled.

Crowley is more level-headed about the situation, saying that Michael has luck with these kinds of things. Echoing to Crowley Rufus’s information that Michael’s injury was lateral to midline, below the belly button, Crowley assures Dean that Michael will be fine. It will no doubt hurt like a bitch, but he’ll be fine.

Dean hasn’t seen Anael since the chapel as she was trying to trace who stole the shiv from Alastair. Cas was stuck in the chapel with the maintenance crew, forced to watch them mop up Michael’s blood.

He thinks that maybe, that’s all the drama they’ll have for the day. Michael will be better by later tonight, Anael will be able to prove who stabbed Michael — though they all already knew, if it wasn’t Alastair, it would be Lilith. He thought that would be it for the day, until Lilith orders Gabriel to leave her and Dean alone in the cell to talk.

Gabriel leaves reluctantly, signalling to Dean that he’ll be nearby.

Alone, Lilith starts, “Alastair doesn’t want to work with me anymore and I have too much supply to just stop, so you’re going to sell it for me.” Instantly, Dean says no, and she doesn’t take it well. “I know you and Michael have something going on, and I know his husband’s upstairs fixing him. You help me get rid of my stash or I go up there and kill them both. They will never see me coming.”

Dean feels dread deep in his gut. “What the hell is wrong with you?”

“Nothing. Everything is fine,” Lilith says. “So what’s it going to be, De Luca? Alastair’s not the only person who knows how to make shivs.”

Dean shuts his eyes and breathes in deep. Cas is gonna be so mad.

**Thursday, 11:39 PM  
** **86 hours**

Gabriel bursts through the medical bay doors, looking around until he locates the bed Michael is in. Adam isn’t there, talking to Dean outside the office. Michael is sitting up, finishing a doughnut that Rufus probably got for him.

“Jesus, Michael,” Gabriel sighs, relieved that he’s apparently okay enough now to enjoy a donut. He hadn’t seen how Michael looked when the shock and pain kicked in but from how it sounded, Gabriel had been scared. “You cannot keep doing this to me, one day you’re gonna give me cardiac arrest.”

“The devil’s getting sick of throwing me welcome parties,” Michael tries to joke as Gabriel stares at him, his face stuck in an expression that is way too sombre for his comfort. “Next time I go’s going to be for good, Gabriel. Can’t cheat death three times and get away with it, right?”

Gabriel interrupts, “Can you stop it? Stop joking around.”

Michael pauses. Then, quietly, he chuckles. “Am I mistaken or weren’t you the comedian between us?”

Unable to stand it any longer, Gabriel snaps, “This isn’t fucking funny.”

That gets Michael to stop and Gabriel continues, like a bullet train that’s gone off the rails, and Michael listens silently like he’s watching it go and can’t look away. “Do you think I find it fun to worry about you? Because I don’t! I _hate_ it, Michael. You cannot begin to imagine what it felt like when I saw you in the laundry room all those years ago and you were barely breathing. _Fuck_ , I was so damn scared. I shouted for help, I tried to get you to wake up and you just wouldn’t move.”

Michael swallows. “Nobody told me you were the one who found me.”

“Well, I was,” Gabriel says. His hands are shaking — his knuckles are white. “And I carried you to the med bay.”

“I’m sorry.” Michael’s chest suddenly feels like it’s caving in with guilt. “I wasn’t aware.”

“Fuck that, we’re talking about you,” Gabriel brushes aside. “You know what you told me the first time you OD’ed when you woke up?” He gives Michael no time to try and recall, echoing his words from nine years ago, “You were shaking and crying, you told them ‘I just want to see him one more time’. And you were so sure you were gonna die, you kept begging them to let you go see ‘him’ but they wouldn’t.”

Michael falls silent.

Painfully, Gabriel says, “You broke my heart, Michael.”

Gabriel knew why Michael and especially Adam were so against the plan from the beginning — Michael had barely survived his time here between spending almost half the time in solitary confinement and cocaine or heroin. He’d seen it himself, it’s why he instantly agreed to come along when he heard that Michael would be going. If Adam wasn’t going to be there, then Gabriel would volunteer to look out for him.

“You’re like my brother, man,” Gabriel admits brokenly. “You can’t keep dying on me. One day, you won’t come back again.”

“You’re my brother too,” Michael says. Gabriel leans over the bed for a hug and Michael opens his arms to accept it, pulling him close in an embrace. “I’m so sorry, Gabriel.”

“Just try not to have any more brushes with death for the rest of your life and we’ll be cool,” Gabriel manages a half-hearted joke and Michael huffs a laugh.

“Adam, I need to talk to you,” Dean says. Adam considers him for a moment before he nods towards the office door. The two of them leave the med bay and into the privacy of the office. Thankfully, Rufus was out tending to an inmate in B block so they had it to themselves. Settled, Dean begins, “First, I want to say I’m sorry. I made a promise to you and I should have kept it.”

“Yeah, you should have,” Adam snaps. “Even if you really needed his help, you shouldn’t have tried to keep it from me.”

Dean nods. “I get that, and I was wrong to do that. I just didn’t want to worry you. I know you love him, I knew you would try and find a way in. Neither of us wanted you to be in here, we were trying to keep you safe.”

Adam laughs sarcastically and it feels cold in Dean’s gut. “Yeah, when Sam kidnapped me and Ketch and Naomi used me as a punching bag, you sure kept me safe.”

Dean has no counterargument to that. They were both his errors, after all. If he couldn’t redo it and take back his mistakes, then the least Dean owed to all of them was his acknowledgement that he had failed them. “I know.”

Leaning in closer, Adam says quietly, “I just want you to know, in case anything else goes wrong, that I may have known you for 6 years, but I knew Michael for 11. I’m sorry, but I will do _anything_ to make sure Michael gets out of here.”

He didn’t say the exact words but Dean knew what Adam had implied. Clear as day — he’d pick Michael over him if it comes down to it. Sure, Dean had been afraid of this choice. In fact, he'd told Gabriel that he thought this would happen but he couldn’t say he didn’t anticipate it. He did know Michael far longer and all Michael had ever done was try to protect him. Dean had him run into danger. He couldn’t be mad at Adam for it, he would have made the same decision in his shoes.

Dean can’t say he didn’t deserve it — it’d be a lie, at least to Dean. Maybe Cas would argue and say Dean didn’t have a choice sometimes and that he did what he could with what he had, has always tried to save everyone, but Dean didn’t feel the same.

Dean draws in a deep breath. “I know. I’ll do my best.”

“You better,” Adam says. “And I don’t need you to protect me. Now go back to your bunk, De Luca.” Adam leaves him to return to Michael’s side and Dean returns to his cell, brimming with all the apologies he had always wanted to give everyone but never got to.

It leaves a bitter taste in his mouth that will never go away.

**Notes for the Chapter:**

> Summary: 9 years ago flashback is Gabriel and Michael in prison discussing Michael's drug habit and Adam. Dean makes a new plan -- escaping through a hijacked supply truck that will come to the kitchen. John Winchester gets killed by Alastair. Lilith ambushes Michael, angry that Alastair wanted to work with him instead of her, and stabs him twice. Michael seeks out Castiel for help and passes out. Lilith blackmails Dean into selling drugs for her in exchange for her sparing Michael. Adam and Rufus stabilise Michael, and Gabriel and Michael have a heart-to-heart. Adam tells Dean that he doesn't trust him anymore.


	5. Day 5: Toast Can't Be Bread Again

**Notes for the Chapter:**

> Sorry for not updating for so long, I was trying to finish this other fic so I can focus on this one and to be honest, I had a little writer's block but! Here it is! It's back!
> 
> TW/  
> Mentions of drugs

**8 years ago**

It’s not Castiel’s first time in prison but it doesn’t mean he can stand being there.

He’s had a break-out plan prepared for a while — knock out a guard, steal the uniform and the gun, take the head CO hostage and forcibly leave. Cliché, but the only plan Castiel could think of that wouldn’t involve murdering someone on his way out. Another inmate tried breaking out last year by sneaking through the sewage. He got caught halfway through the pipes.

Least to say, he’s not very confident in his chances. He might just wait out his last year instead. It seems like the safest bet.

A part of Castiel wished that Gabriel was in the same prison he got sent to but of course, his luck simply isn’t good enough for his brother to be there. He knows Gabriel’s sentence ends in two years and he desperately hopes he’s doing well.

When he gets out next year, Cas already has plans for a new heist — a small store, small target. The police will take time to arrive; he’ll have time to escape and plan another mini heist. He’ll slowly build back up to Champs-Elysées level. A better person would stop completely but the adrenaline that rushes through him when he steals... nothing compares. The thrill of it is impeccable and if it were up to him, he’d never stop.

He loved the pristine tiles of jewellery shops, the quiet tinkling of expensive diamonds. Now, he stares at concrete walls and listens to angry men get into fights across the block.

Cas really hopes that when he gets out of here, that things will go exactly the way he wants them to — a successful small-time heist to get him back in the game. He doesn’t need more trouble.

**Friday, 9:23 AM**  
**96 hours**

Dean feels a little disheartened by what happened the day before. It’s a huge setback, for sure, though it does give Michael a reason to leave any time without suspicion. Of course, this means that Adam took the first ticket out and demanded that Michael be moved to an actual hospital.

The stabbing has put the rest of the Dalís at unease — Adam obviously has his doubts with what little trust he had in Dean. Gabriel seems to be on the fence, refusing to take any sides in the whole ‘should we let Dean be the leader’ debate. Anael is as tense as she was from the start. Dean feels like Crowley and Meg are hiding things from him and Mick, of course, has been radio silent since he's not needed in the plan yet.

Cas, though? Cas has been quiet. Dean hasn’t seen him since the Michael and Lilith incident. To be fair, Dean had been promptly sent back to his cell by Adam after Michael was confirmed stable. Gabriel came back about an hour after and told him about his history with Michael. At least now, Dean understood a little better.

Michael’s experience in the criminal life did offer Dean some sense of security but he knew letting him leave the prison was the best choice. He cared for Michael as a brother-in-law, and he certainly didn’t want to get any further on Adam’s bad side than he already has.

Dean has a few problems to deal with right now; Ensuring that Crowley continues to stay quiet, making sure he doesn’t lose his brother and the packet of cocaine in his pocket that Lilith gave him.

Neither Adam nor Gabriel will have a good reaction to it. Crowley will be stuck in the same room as Naomi for a while which makes him a terrible choice. It leaves Anael as the only one who can help him so he looks right at the camera, knowing Anael is watching and nods once to his cell. Gabriel’s gone, probably talking to Cas.

Anael arrives a few minutes later, concerned. “What is it now?”

“Lilith is going to make me sell drugs,” Dean explains calmly.

Anael’s eyes widen and she hisses, “First Michael, now _you_? Dean, you _cannot_ do that shit! We’re supposed to get out of here!”

Dean feels sick as he explains the situation in a hushed voice, “You think I want to do this? If I don’t sell these for her, she’ll kill Michael for real. He’s not being guarded in that hospital and she can leave the prison any time.”

“That’s the hospital and Adam’s problem!” Anael glances out of the cell at an inmate passing by, trying to school her face into something more neutral to not grab attention. “Dean, don’t be a fucking hero. That’s not who we are. Just do the damn plan and get us out of this place. We don’t need Lilith’s drug ring on top of it. What if you get caught and get thrown into solitary? What the hell do we do then? Solitary can go for over a month.”

“I’m trying my best,” Dean snaps. “Look, I said I’d get all of us out of here and I’ve kept that promise twice now, right?”

“Once for me,” Anael corrects. “And you never got Bela, Balthazar and Benny out.”

Dean grimaces and says, "And I'm sorry for that, okay? I already said that I'll never move on from that. But the rest of you, I got you out. Look, if you're this unhappy with the plan then just walk out right now, get on the next flight back to France."

Sure, has Anael lost most of her liking for Dean? Yes. But she did still like everyone else that’s there and she didn’t feel like leaving them behind again.

“I’m not leaving,” Anael says. “But I’m gonna need you to get your shit together. Look, I'll get rid of the coke. You stay out of Lilith's way. We need a plan for if she comes back again, what is it?"

Dean thinks it over before he says resolutely, “If she comes for any of us again, especially Michael or Adam, we’ll kill her.”

“Good plan,” Anael says. “I’m sick of her.”

**Friday, 12:38 PM**  
**99 hours**

Dick Roman’s office is considerably spacious with a large mahogany table that sits right by the windows, framing Roman with light that gave him the ironic look of a saint. He’s far from it — Roman plays the role of an upstanding warden of his prison but he dealt too deep in the underworld.

It’s also ironic how much safer Dean feels in this office than outside. He isn’t that much secure in here with Roman than he is with people like Alastair and Lilith. Yet, being in the office feels like taking a breather.

“I’d say welcome, but then I’d be pretending,” Roman says, though he gestures to the seat across from him before waving Benjamin off. “Close the door on your way out.” Benjamin leaves them alone to talk and Dean sits — Roman may not be so welcoming but the chair certainly is.

“Thanks for letting me come here,” Dean says.

Roman’s eyes narrow. “Make no mistake, Winchester, you’re only here because I have questions.” He leans across the table and folds his arms, his expression twisting into one with a grievance. “You either answer my questions or you get the hell out of my office right now.”

Dean sighs, deciding that his favours with Roman are more important than secrecy. “Fine. What do you need to know?”

Roman comically pulls out a list from his drawer — clearly, he’s been waiting for a chance to interrogate him — and starts, “One; why did Alastair kill your father?”

“I don’t know. I think John owed him something,” Dean answers, shrugging. “I tried keeping my distance from him so... Can’t help you too much there.”

Roman huffs, unimpressed. “Drug money, I’m guessing. That’s what Alastair’s known for.”

Dean’s eyebrows raise slightly in question. “You know what he does and you let him do it?”

“I sell weapons, you think I care?” Roman replies with disinterest. “Two; Anael Jo and Michael Milligan. You put in a favour for me to hire them and now one of them is in the hospital. Are you aware that that puts a spotlight on my prison? Makes it very difficult to handle my business discreetly when authorities are examining it, so you better explain.”

“They’re my... they’re with me,” Dean says, hesitant to even use the label of ‘friends’ or ‘family’ anymore. “Your CO, Lilith, is Michael’s sister. They don’t have a good history and she acted on it.”

Roman exhales loudly through his nose, clearly annoyed by the situation. “Well, I can’t have her running around stabbing her coworkers.”

“So you’re going to fire her?”

“What? No,” Roman says, bewildered. “Neither Michael nor Nurse Milligan is here anymore, therefore she’s no longer a concern for you. She’s been a good CO up until you people showed up, why would I get rid of her now?” Dean has at least ten reasons why she shouldn’t continue working here but if Roman hasn’t bothered stopping Alastair, he doubted he’d listen to those reasons. “Three; That FBI agent, Naomi Intel. She worked your Dalí case twice, didn’t she? Why the hell is she here?”

"She wants Crowley to tell her about the heists," Dean explains.

Roman presses his lips together. “That can be a problem, can’t it? Well, you have three favours left, what are you thinking? A lot of prisoners here will gladly rid you of an FBI agent.”

As tempting as it sounded, Dean knew killing Naomi will only bring them more agents and more problems that are frankly not worth the effort. Leaving her here and having to trust Crowley to really not rat anyone out will have to do. He shakes his head, saying, “I want to cash another favour in for a different thing.”

Roman rolls his eyes and nods. “I should never have let you get these favours to hold over me. What do you want?”

“Put me and Gabriel Novak on kitchen duty,” Dean says.

Roman looks up, suspicious. “MacLeod’s on kitchen duty.”

“Yep.”

“Well, a favour’s a favour. Two left,” Roman says, resigned. “I have one more question; You’re trying to bust Crowley out of death row, aren’t you?”

Dean can’t lie or he’ll lose the last two favours and he knows Roman isn’t stupid. “Yes.”

Roman nods once. “Appreciate the honesty. I’m inclined to admit that your heists impressed me, so I’m also inclined to overlook this breakout attempt. Do what you want but if you get caught by Intel, you get caught. I’m not involved. Are we clear?”

“Crystal. I've got one more favour."

"What is it?"

"If anything goes wrong, if I get caught," Dean says. "I need to get sent to _your_ prison. In return, I have some good contacts looking for an arms dealer."

Roman raises an eyebrow, contemplating it, but he nods. "Alright. Strange request to stay here, but alright. That leaves one more favour. Anything else?"

"No."

“Then close the door on your way out,” Roman says, echoing his words from earlier. “Good talking, De Luca. Say hi to the husband for me and give the Milligans my good wishes.”

**Friday, 2:41 PM**  
**102 hours**

Cas still feels protective over Gabriel despite being the younger of the two. When he’d heard both Dean and Gabriel were in prison, it was a no-brainer to go in. He didn’t expect them to talk so little when he first arrived but figured between inmate work assignments, strict schedules and his own duties as a chaplain, there really isn’t much time to interact with his brother. Talking to Dean is rare enough as is.

Obviously, it’s a welcome sight to see Gabriel without anyone dying around them.

“Hey, little bro,” Gabriel greets, keeping his distance from Cas so security cameras won’t think them suspicious. He sits down on one of the benches, smiling at Cas. “Must be peaceful down here.”

“It’s peaceful as much as it is boring,” Cas admits. “I do like a little more excitement.”

“I’ve got some drama from upstairs if you want excitement,” Gabriel offers. “So your husband and his bro? Not doing so well. Kinda stressing Dean-o out, honestly. Anael’s got her hands full being basically Dean’s second-in-command. Crowley and Meg are being sneaky and, between you and me, Dean’s a little anxious about this plan now. He’s also worried about how Sammy’s gonna react once he finds out where he’s been.”

Cas turns to Gabriel, concerned. “Why didn’t he tell me any of this?”

Gabriel shrugs. “Probably didn’t want you to worry any more than you already are. So you didn’t hear this from me.”

“Well, thank you for telling me either way,” Cas says, sitting down in the bench next to Gabriel’s. Even if he hadn’t known what Gabriel told him, he can tell troubles have been eating away at Dean’s mind since his arrival which is the only reason he’d agreed to stay out of the plan until Dean handled it and got himself, Gabriel and Crowley out. “What about what happened with John?”

"Doesn't bother him that much, I think. If it is, he's not tellin' me," Gabriel answers. "Mostly, he just spends his nights mumbling the plan to himself, trying to tie up all the loose ends before he falls asleep."

“I should talk to him,” Cas mutters to himself. None of it can be easy — prison is hard enough as is and on top of seeing his (albeit hated) father murdered, having to see his brother-in-law in such bad condition and watching the trust in him fading from his half-brother's eyes can't be easy. In fact, Cas can see everyone losing faith in Dean.

Perhaps they never did trust Dean Winchester; they trusted _Kansas_.

Kansas was a genius, a criminal with a mind that could defeat any enemy; a swift hand that crushed every problem that came their way. Kansas was the only source of stability of the other Dalís' lives since the start of this mess, the only one they could count on to protect them. He was the promise of a better future, a new beginning; for some, the only shred of hope they've had in years. He’s the sand at the top half of the hourglass, when you see that time is moving but there is still so much of it left.

Kansas is a fairy tale. Dean Winchester is just a man.

There’s only so much he can handle on his own.

**Friday, 5:23 PM**  
**105 hours**

Anael has tried her best to keep low by doing her shifts, minding her business. Sticking close to Hannah does help — they’re a pretty relaxing presence to be around — though she can’t help but feel envious that Michael got to leave. Adam insisted on staying so he can watch over them as he’d apparently promised Michael, which means his watchful eyes are really over just Gabriel.

What makes things a little tougher is the FBI agent walking around. She knew Crowley from the first heist and was unsuccessfully interrogating him. She knew Dean and Adam’s face as well and if she chanced upon either of them then the “game” is over. 

Plus, Dean’s plan is semi-stable at best. Anael isn’t exactly confident that she’ll remain prison-free. Ruby assured her that it’ll be fine. Anael believes her partially.

She’d only been on her way to her next station when Naomi pulls her aside to say, “Hello, Paris. We’ve never met face to face before, have we?”

Anael freezes. “How do you know who I am?”

“Let’s say someone sung like a bird,” Naomi smiles, gesturing to one of the smaller rooms. “Can we talk?”

Unsurprisingly enough, Naomi refuses to say if it was Crowley who gave up a few names. Originally, she only knew Crowley, Meg, Sam and Adam and she’ll recognise Dean, Mick and Jo. Now, she also knows Anael.

“If you tell me who else was involved in the heists, I’ll let you go,” Naomi offers. “This deal isn’t easy to get and I’m handing it right over. If you’re smart, you’ll take it and walk out of this room with no consequences.”

“I don’t know who told you I’m Paris but I’m not them. I’m not a snitch,” Anael sneers. “You’re not getting anything from me.”

“That’s fine.” Naomi nods understandingly. “I’ll just note down to also arrest Ruby for assisting in hiding a criminal from the authorities.”

Anael’s head snaps up, eyes wide. “She didn’t do anything.”

“She housed you in France instead of reporting you, Anael. She hid you from Interpol when they were looking for anyone involved in the Dalí heists,” Naomi says, her voice irritatingly smooth. “Even you have to know that’s illegal.”

“What do you care about what’s legal or not?” Anael challenges. “You have blood on your hands. You killed the ones that didn’t do anything.”

“Didn’t do anything? They broke into the Bank of America. Anael, _they stole from the country,_ ” Naomi points out, sitting on the edge of the table to look down on her. “Let’s not forget your own non-Dalí related crimes. Anael Jo, con artist. Never landed in jail but you have your work cut out for you. It took a lot of digging to find anything. Killed a man ten years ago for?”

Anael works her jaw. “He shot his wife. I shot him.”

“Righteous,” Naomi says, obviously unimpressed. “Look, I don’t have much time because MacLeod will be dead in less than a week. Do me a favour and give me just one name that I don’t already know. I know you’ve been keeping track.”

“And I told you, I’m not giving up anyone,” Anael says bitingly. “Now can I go?”

“Fine,” Naomi relents. “But if I end up unable to find who started all this, I’ll be coming for you and your Ruby, CO Jo.”

**Friday, 7:05 PM**  
**107 hours**

By Gabriel’s request, Dean headed down to see Cas after having his dinner — granted, Dean was so excited to finally have a pocket of time to see Cas that he'd practically shoved the half-cooked dinner down his mouth so he could leave as soon as possible. Cas didn't have to know that.

Seeing Cas at the altar is like a breath of fresh air.

“God, I want to hug you so bad,” Dean says heavily.

Cas walks over and gently pulls Dean into an embrace. “I’m sure they can let one hug go. Hello, Dean.”

“Hey, Cas,” Dean says, feeling the relief he’s been begging for rush through his body. “I’m starting to think I should never have answered the door when Rowena knocked.”

“Perhaps we should have stayed in bed the day Meg found us in Italy. We’d have avoided all of this.” Cas huffs a half-hearted laugh. “It’s all ‘what-if’s now.”

Cas reluctantly pulls away, knowing that a hug that lasts any longer will look suspicious, and says, “Gabriel told me about your worries.”

“I told him not to —"

“ _Dean_ ,” Cas cuts over. “I’m your husband. You know you can tell me anything.” Dean slowly nods and sits down, shifting inwards so Cas can sit next to him. “We’ll handle this one by one, okay? So what do you want to talk about first?”

“Adam and Michael,” Dean starts. Given that Michael’s no longer in the prison and therefore effectively excluded from the plan, Cas guesses that Dean is starting with the least critical problem first. “It’s my fault this happened to Michael, I should have used one of my favours to get Lilith out of here before anything happened and now Adam’s so close to hating me for not doing that. Sam’s gonna be really mad when he realises what we’ve done.”

“Adam will come around eventually,” Cas assures. “He's protective, of course, so I think it's just his rage speaking right now. Once this is over, he'll be back to normal. And for Michael, you couldn't have expected Lilith's madness. It's not your fault and since he's not here anymore, she's the least of your worries now."

Dean nods, drawing in a deep breath. Clearly, his assurances were helping even just a bit. "Crowley and Meg are both being quiet."

"Might simply be your paranoia. It's been a while since you saw them, you're anxious about your brothers. It makes sense."

Dean suddenly turns to him, his face twisting into something broken. “Cas, I’m afraid that I’m becoming more Kansas than Dean.”

Cas frowns. “What are you talking about?”

“I barely remember who I was before I picked that city and started planning the Bank of America heist,” Dean confides. “I don’t remember what my mom’s favourite song was. I don’t remember when exactly John left us. I don’t remember what Sam looked like when I left. I feel like, slowly, I’m losing the parts of me that are still me, and all that’s going to be left of me is Kansas.”

Cas reaches over to take Dean’s hand in his. “If you ask me, you’re still Dean. I don’t think Kansas is consuming you. Maybe one day, when we’ve put all the Dalí business behind us, you can go back to how you were before it started.”

“That’s the thing, Cas. We can’t ever go back to the way things were. We gotta accept that, no matter how much we wish for it,” Dean says. “Toast can’t be bread again.”

Cas wished he was wrong.

**Friday, 10:57 PM**  
**110 hours**

Meg arrives at the phone booth that Anael had asked her to meet her at when the sky is dark. She'd been doing her best to give Dean's questions satisfactory answers but she can tell he's getting restless at them as they get vaguer and vaguer. When Anael asked her to come take some baggage off of her hands, Meg hopes that showing up will at least provide some assurance to their 'leader'.

“Meg!” Anael calls out, walking over to her. She’s still in her CO uniform, though she has a fashionable maroon coat over it, her red hair flowing behind her. “It’s good to see you.”

“You too.” Meg smiles. She hopes it looks sincere.

“Need you to get rid of this, it’s driving us all crazy,” Anael says, handing her a bag of white powder. “Michael’s got one insane sister.”

Meg huffs a chuckle, tucking the baggie into her jacket. “From what I’ve heard, she does sound like a handful.”

“Thanks for taking that for me,” Anael says. “How’re things on you and Mick’s end?”

“We’ve got the transport for the escape handled,” Meg says. “Pretty likely that you’ll see Jo and Ash pick you up in the food truck that day, so keep a lookout for the drivers.”

“Got it,” Anael nods. “Well, I gotta go — night shift — but I'll see you again when this is over. Goodnight, Meg."

Meg gives her a hug. "Goodnight, Ana."

She hopes it makes up for all the trouble.


	6. Day 6: She Deserved To Die!

**Notes for the Chapter:**

> TW/ 
> 
> Violence/weapons/murder at 3:29 PM  
> Mention of dead body at 7:13 PM

**7 years ago**

Once they’d split the loot between them, the Dalís headed in separate directions, agreeing to meet again next year to check on one another. Dean, Cas, Sam and Jess went to Italy, of course. Anael’s not exactly sure where Gabriel and Crowley went after. Adam and Michael went back to Detroit. Meg went to Madrid to live the life she and Bela had planned as far as Anael knows. 

Anael herself goes to her namesake — Paris, France. The thing is that she didn’t know anybody in Europe except for Meg in Spain and a few others in Italy which means France is a new start. She converted some of her share of the money to euros and spent a portion of it on all the designer clothing she’d wanted.

She’d visited Champs-Elysées, smiling at the memory of how Cas had robbed this place before. Clearly, it had time to recover from the loss incurred by Cas, and it looks as if he’d never gotten his hands on their treasure.

There, she saw the most beautiful woman she’d ever seen. Going up to her, Anael learned that her name is Ruby and that she was looking for a roommate to split the rent with. Ruby had an apartment in a much nicer part of the city compared to Anael’s and plus, gorgeous roommate, so it seemed like an easy decision.

Anael volunteers to be Ruby’s new roommate.

Moving in is simple enough; Anael didn’t have too many personal things she wanted to bring over to Ruby’s. They set up Anael’s room for an hour before deciding that it’s much easier to just share a room.

Things just built from there. Anael fit right into Ruby’s life perfectly as if there’d always been a space waiting for her. Anael learned French bit by bit, the more she heard Ruby speaking in the language. In return, Anael taught her about the things she’d learned through crime — how to detect a good diamond, how to case a scene.

Half a year after moving in, Anael told Ruby that she was part of the heist on the Bank of America. She thought Ruby may find it appalling but, surprisingly enough, it got Ruby more interested in her. She wanted to know everything about the heist, what happened inside that never got documented on the news.

In fact, Ruby promised, “Interpol is looking for you but you can stay here as long as you need. You’ll be safe here.”

That’s the first time Anael kissed Ruby, and the first time Anael ever felt happiness without crime.

**Saturday, 8:23 AM**  
**120 hours**

Dean's in a good position right now, as far as the plan goes. After talking it out with Cas the evening before, Dean had decided to throw all his energy and concern into getting himself, Gabriel and Crowley out either today or tomorrow and that everything else would be a problem for another day. His relationship with his brothers, the dues he has to pay, the tracks he will have to cover. He'll handle them at another time.

Of course, because of Roman’s favours, Dean had secured Gabriel and his job postings in the kitchen with Crowley so that they can escape through the stock delivery van. Meg told Anael last night that Jo or Ash will probably drive the van and help them get away, though he woke up to a text update from Meg saying that Dorothy may be the one instead.

All in all, Dean felt good about his chances for now. It already feels like prison will be out of sight and mind soon. Cas was right, being here is awful, regardless of if he was getting out in a few days or not. He got why Cas, Michael and Crowley hated it so much. Even Gabriel didn't like it there, no matter how at home he acted about it.

With John dead, Dean hopes that can serve as some kind of cushioning for the impending rage from Sam he knows he’s bound to receive once news of this ‘heist’ gets to his ears. The heist on the Bank of America, the heist on the Diamonds Factory and now, essentially “stealing” Crowley from the Potosi Correctional Centre. He’s doing a bad job of being a good brother.

At least, for now, it’s the calm before the storm. Roman doesn’t care enough for his prison to try and find out Dean’s plan to free Crowley and Naomi seems to be distracted by interrogating him.

The kitchen is a much calmer place to work compared to his previous posting. Yes, it may be a little hard to cook when sharp objects are prohibited, but it’s a better situation. Nobody dares touch the cooking inmates because they don’t want shit in their food. Dean’s heard the stories.

Dean can only hope that the good luck doesn’t run out when they’re this close to getting away with it.

**Saturday, 11:37 AM**  
**123 hours**

Crowley’s more than sick of Naomi’s face by now, yet he’s still being subjected to the sight of it every day he’s been out of solitary. Today is no different; Naomi continues interrogating him about the heists, thinking she can pull information out of him.

Although Crowley had originally thought it best to give up everyone else and grant himself immunity, Dean’s threat did end up bearing some weight. Dean hadn’t killed before but he’s surrounded by people who have — Michael, Adam, Castiel — and if he did give up names, everyone else will be after him. Anael, Meg, Dorothy... the list can go on and on. The fact is that he will not last one day alive once he gives them up. He'll be dead the moment he stepped out of the building.

The Dalís may be a family but almost all of them would rather kill each other than give themselves, or the ones they loved, up. It’s no secret that Cas will kill to ensure Dean’s safety, or that Michael would kill for Adam, Meg for Bela, Anael for Ruby, Dorothy for Charlie.

Long story short, the Dalís are a bigger threat than Naomi, which is why when Naomi asks him for names once more, Crowley denies her demands. However, today is different. Today, Naomi concedes.

“Fine.” Naomi straightens up, her face alarmingly calm. “Don’t tell me anything.”

Crowley narrows his eyes up at her as she paces around the table. “What?”

“I already have quite a few names from the heists. You, Meg Masters, Adam Milligan, Sam Winchester. The deceased Bela Talbot, Benjamin Lafitte and Balthazar Freely,” Naomi points out, circling around Crowley’s seat. “Recently, one of your own gave up Anael Jo and her little Parisian lover, Ruby. That same person told me just this morning about someone named Michael. Ring a bell?”

 _Someone gave up Anael and Michael?_ Crowley almost laughs. Whoever did that has got some guts, he had to admit. If they found out who ratted them out, the informant will be dead before morning.

“I’m inclined to not provide any answer, whether it does or doesn’t,” Crowley answers. “What does it matter if you have a few names, accurate or not?”

“This person didn’t give me these names out of good will,” Naomi begins, sitting down again across from Crowley. “It’s part of an immunity deal. They’ll be let off the hook as long as they give me information about the heists. But here’s the catch, MacLeod. I’m giving you the chance to steal this immunity deal from them.”

Crowley and Naomi make eye contact for the first time since he stepped into the interrogation room. Her eyes are filled with cold glee, like she’s cornered him in a game of one-sided chess.

“What, by giving you more information and have all the Dalís after my head? No thanks,” Crowley says.

“I’ll put you in witness protection if you comply,” Naomi says. “You just need to tell me the names of everyone else or, if you truly are concerned about your safety, the only name I really want is Kansas’s.”

Crowley looks away to think. He can argue for immunity for Rowena as well as the others whose identities have been exposed. He just had to give Dean up — somehow, it's easier said than done. Even if they successfully capture Dean and imprison him for life, Castiel is admittedly more terrifying than Dean is. For one, he has no qualms about murder. For two, Castiel has quite a number of contacts in the criminal underworld, much like Dean, Crowley, Anael and Michael. He can easily find out it was Crowley who sold Dean out and, well, he knew how that would end for him.

Angeles can be one scary motherfucker when he wants to be.

“I’ll give you until tomorrow to think about it,” Naomi says. “But you are running out of time, MacLeod. You have eight days left to live so I suggest you hurry up.”

Castiel is feeling beaten down at best.

It hurts to see Dean be so torn up about his identity and to have his insecurity about all his relationships laid out in the open without knowing how best to help him. At the very least, he’s secure about the fact that they will be back in Palermo by tomorrow evening, more or less, and they’ll have all the time in the world to deal with Dean’s personal problems.

For now, as much as it pained him to do so, Cas knew they had bigger fish to fry than Dean’s identity issues.

One problem being Crowley and the new information he has presented him. “Naomi offered me an immunity deal today.”

“Will you sit down?”

Crowley obeys, sitting down on the closest bench to him as he begins talking, pretending to be in prayer. “She only wants Dean. The rest of us can go free as long as he’s caught.”

“Not an option,” Cas instantly rejects.

Crowley clicks his tongue in annoyance, sparing a glance up at him. “You didn’t even think about it.”

“He’s my husband. There’s nothing to think about, the answer is no,” Cas replies. “Don’t tell me you’re considering it.”

“When you have only eight days left before you get your brains fried, it tends to put your priorities in order,” Crowley says patronisingly.

“Still no.”

Irritated, Crowley asks, “You’d rather all of us go down in Dean’s place? You and perhaps Samuel would be glad to do so but I refuse to. So will most of the others, I’m sure.”

“I’m not asking you to sacrifice yourselves for Dean,” Cas insists, his annoyance growing with Crowley’s. “I’m asking you to not sell him out with how much he has given us in the past years. We all started with nothing, now we have everything we want and more. We’re okay now because of him. Is that not reason enough? Are all of you really this selfish and ungrateful?”

Crowley smiles tightly. “My respect lies with the city-named commander with the Dalí mask who walked right into a police tent and tricked them into saving his life. My loyalties lie with myself.”

Cas scoffs, shaking his head, before he slams a hand down on the bench’s back and leans over to Crowley. “You will not give Dean’s name up.”

“Or what, Angeles?”

“Or I will hunt you down. The moment you step out of this prison, you will never be safe again,” Cas says lowly, his glare digging into Crowley. “Dean Winchester is everything to me. If Dean goes to prison or gets a death sentence, I will find you, no matter what dark corner of this planet you’re hiding on, and I will make your life a living nightmare. Joy will be a stranger to you. You will never remember your mother’s face. I will make you wish you were dead.”

Crowley inhales. “I’m not afraid of you, Cas.”

“I never said you were,” Cas says. “Get out of my sight.”

**Saturday, 1:42 PM**  
**125 hours**

With news that they’re likely leaving tomorrow, Adam cannot be more relieved. He’s hated every minute in prison. Not so much for his own experience — Rufus is good company and most of the inmates that get sent to the medical bay just leave him alone to appreciate the quiet that they don't get in gen-pop. Because Michael's no longer there to have lunch with him, Rufus has lunch with him instead and today, CO Johnson joined them. They're really friendly, which left Adam in a pretty good mood.

Thankfully, they left Rufus in a good mood as well, because Adam is given the chance to go see Michael at the hospital nearby with what little time they have left of their lunch break.

Michael is doing a lot better there than in the prison’s medical bay which relieves Adam immensely. They don’t let him stay overnight so Adam can only try to see him for a few hours and then wait until the next day. At least they’re leaving soon; they’ll be back in Detroit by tomorrow night.

“Hello, Adam,” Michael smiles as Adam walks in, pressing a kiss to his forehead. “How’s work?”

“Same old,” Adam says. “We’ll be gone by tomorrow.”

“Thank God,” Michael sighs. Adam chuckles, settling in the chair at the bedside.

Adam asks, gently lifting up the blanket to check his bandages. “How’re you feeling, Mike?”

“Better.”

“Good.” Adam smiles — seeing Michael’s face is a relief, especially when it’s not dripping with agony as he bleeds out on the floor. “At least you’re safe here.”

Michael nods once before his expression turns serious. “Is Lilith leaving you alone?”

“So far, yeah,” Adam answers. “She’s just been keeping to herself. I think she doesn’t wanna draw attention to herself so soon after getting you.”

“I’d do the same,” Michael says, shrugging. “As long as she’s staying away from you. If she hurts you, I’ll kill her, I don’t care how hard it’ll be.”

“Mike...”

Michael leans over from his place in the bed, tucking one hand under Adam’s chin to gently turn his gaze towards his own. “Hey, promise me you’ll be careful. I can’t look out for you in there.”

Adam brings Michael’s hand up to press a kiss to it, mumbling, “Yeah, I promise.”

“Are you coming back here once you get out or do you want me to meet you somewhere with a car to leave?” Michael asks. He tentatively touches his bandages and winces slightly. “I’m already feeling much better.”

“No, you don’t.” Adam frowns, unconvinced. “I’ll come back here. Since I’m an employee, nobody will be hunting me down if I leave. You just stay here and wait for me.”

“Okay, okay,” Michael concedes. “Be safe.”

“I will.”

**Saturday, 3:29 PM**  
**127 hours**

Anael doesn’t have a good feeling about today.

Maybe it’s paranoia born out of never having a moment to breathe every time she does something with the Dalís, but she doesn’t have a good feeling. Though the day has been going quite well so far, something always goes wrong. Prime example? Her name being given up. She can't imagine who would do that; she has some people that she's certain would never do this.

Dean and Cas, for two. Their brothers and their partners wouldn't, which rules out Adam, Sam, Gabriel, Michael and Jess. Charlie wouldn't, she knew what hell she'd incur on herself, so neither would Dorothy.

Dean and Cas, for two. Their brothers and their partners wouldn’t, which rules out Adam, Sam, Gabriel, Michael and Jess. Charlie wouldn’t, she knew what hell she’d incur on herself, so neither would Dorothy. Jo likely won’t, just because of how long she knew Dean and Sam for. Therefore, Ash wouldn’t out of respect for Jo. Eileen didn’t seem like the type and Anael liked to think herself a good judge of character. The Banes twins from the first heist didn’t know any of them and were definitely not the informants. Giving them up would entail giving himself up as a national traitor, so Mick is out. That leaves Crowley, Rowena and Meg.

Before Anael has any more time to think about it further, Anna interrupts her train of thought. “Hey, did you hear anything about CO Milligan?”

“His husband says he’s doing well,” Anael answers, glancing over at the other redhead.

Anna smiles slightly, nodding. “That’s good. I didn’t talk to him much but he seemed like a good guy.”

 _If only she knew his history_ , Anael thinks to herself. “Yep.”

“Who do you think did it?” Anna asks. “I heard from Benjamin that the weapon belonged to an inmate. Alastair White, I think?”

“Why only suspect the inmates? Could be a CO,” Anael mutters. “Some of the convicts here aren’t that bad.”

Anna raises an eyebrow. “They’re criminals.”

“You think that Alfie kid could hurt Michael like that?” Anael questions incredulously. “Even you have to admit a lot of the inmates won’t stand a chance against him.”

“That’s true,” Anna admits just as Anael catches something on the cameras. She leans closer to get a better look.

In Dean and Gabriel’s cell, the two are slipping out as Lilith makes her way down the hallways, a mission clear in her stride. The two men end up going down the same hallways as Lilith does, if only a little behind. Anael’s gaze follows Lilith as she enters the medical bay quietly.

In the medical bay, Adam is there alone. Anael faintly remembers Rufus leaving ten minutes before. Adam goes through folders in the office as Lilith looks around, moving to one of the bedside tables to grab what looks like a scalpel. Anael tenses up, her eyes darting across the screens to relocate Dean and Gabriel. They’re almost at the medical bay.

“Hey, Anna, can you get us some coffee?” Anael asks, twisting in her seat so her body covers the monitor that displays the medical bay.

Anna nods, standing. “Do you have a preference?”

“Surprise me.” Anael smiles and waves once as Anna gives her a thumbs up, leaving her alone in the room. Once Anna is gone, Anael swivels around in her seat to watch what’s going on in medical. “What the hell are you doing?”

She watches, anxious, as Lilith creeps over to the office door, opening it. She assumes it’s silent as Adam doesn’t react to the door opening, still distracted by the folders. Lilith lifts up the scalpel, inching closer towards Adam. Anael would go but she knows she’ll never make it in time — she can only hope Dean and Gabriel get there before she makes her move.

The medical bay door opens and Gabriel checks if Lilith is in the main area before Dean gestures to the office door. Gabriel holds up a crowbar left by one of the inmates that had been asked to fix a cabinet there. Dean takes the crowbar from him and goes straight for the open office, peeking in to see Lilith just as she brings Adam into a chokehold.

Adam slams his elbow into Lilith’s side but she grips him harder. The scalpel in her hand slides across Adam’s arm and Dean rushes over, raising the crowbar just as Lilith turns around to face him.

Anael’s eyes widen. “ _No_.”

"Dean, you sure Crowley isn't lying?" Gabriel asks, following Dean as they make their way to the medical bay.

"I don't know why he would lie about this," Dean says. They make a turn as Dean points out, "If he even jokes about Adam's safety, Michael will kill him himself."

Gabriel almost chuckles. "That's true."

“He always been this way?” Dean asks, making sure Lilith hasn’t spotted them before moving forwards.

“Scary?” Gabriel jokes, following him. “Yeah. You should’a seen when he killed that one guy.”

Dean holds up a fist to tell him to be quiet when he sees the signboard for the medical bay. When the coast is clear, Dean and Gabriel quietly run over and go through the door.

The bay is empty, spare the office door being open. Dean gestures towards the office and Gabriel crosses the room and finds a crowbar. He walks over to pass it to Dean who has his stare fixed on the office.

Crowbar in hand, Dean approaches the office door and looks in. His heart instantly drops when he sees Lilith pull Adam into a chokehold. Military training kicks in and Lilith moves quick, reacting to Adam hitting her with his elbow by cutting him with her scalpel.

“Lilith, stop!” Dean calls out, raising the crowbar.

Lilith turns around with a twisted smile. All Dean notices is the blood on Adam’s arm. “De Luca! Aren’t I doing you a favour?” 

Dean drives the crowbar straight into Lilith’s head.

Lilith crumbles to the floor, almost mockingly quiet in the medical bay, and Gabriel reacts first. He bends down to get a tarp under her head so blood won’t get all over and incriminate them.

Adam stares, frozen in his spot. “Did you just kill Lilith?” Dean doesn’t answer and his eyes start darting around the room, looking for a solution where he doesn’t get caught for this. Adam grabs his arm and whispers, horrified, “Dean, what were you thinking?”

“I wasn’t!” Dean replies impatiently, wrenching his arm out of his grip.

Gabriel looks up at him from his place on the ground. “What did you do that for?”

“She deserved to die! She was going to kill Adam and Michael!”

Gabriel shuts right up — it’s a point he can’t argue. Adam gestures to Gabriel to tend to Dean as he takes over in attempting to reduce Lilith’s bleeding out. Gabriel stands, walking over to Dean to rest a hand on his arm. “Dean, breathe.”

Dean drags in a shaky breath. It’s harsh in his throat. “Gabe, man, I just fucked everything up.”

“It may not be too late. We can still leave by tomorrow as long as the body’s gone by tonight,” Adam insists, looking up from the floor. Sure, he’d been mostly pessimistic during the mission but when the leader’s down, someone has to keep up morale. “I can arrange something with Michael or Meg. Anael and I can get rid of the body. Unless you can cash in another favour.”

Dean did have one last favour left but he had a feeling he’d need it for something. His intuition was rarely wrong. Panic about his first kill begins to seep into his nerves and he schools his face into something more neutral, forcing himself into the Kansas persona. _Pretend you have your mask on. Pretend this orange jumpsuit is red. The sound of the printing press running. Cas — no, Angeles._

“Get the body out of the building before tomorrow starts,” Dean says and Adam nods, waving to Gabriel to help him as Dean begins plotting. “We’re leaving tomorrow as soon as everything is settled. I’ll get Dorothy and Jo to pick the three of us up in the truck. We need to leave before evening."

“Glad to have you back, Kansas,” Gabriel says lightly, helping Adam move the body to one of the gurneys out of the security cameras’ views.

Dean exhales quietly. His hand is still shaking.

**Saturday, 6:01 PM**  
**130 hours**

1 minute after 6, the lockdown protocol is implemented.

Dean’s heart has been running at a thousand miles an hour, thinking about how he’ll handle this. A dead CO is infinitely more cataclysmic than a dead inmate, especially a valued correctional officer. When John was alive, it wasn't like he was particularly well-liked by the inmates or officers and neither did he bring anything to the table like Alastair with his narcotics and Asmodeus with contraband. He didn't have any living family that cared enough. His death was swept under the rug and he was buried in the cemetery nearby.

Lilith Monroe, though? Dean knew Roman valued her as an employee, to the point that he still didn’t want to fire her after her incident with Michael. She had power here, undeserved power, and now she’s dead and her blood is metaphorically on Dean’s hands.

Anael and Adam volunteered to take care of the body. Gabriel readily agreed to serve as his alibi — Cas would have volunteered if he hadn’t been under surveillance and very clearly been with only Alfie and some other inmate during the time of Lilith’s death. Crowley said he’d make sure Naomi doesn’t tie her death to him and Anael and Dean is checking with Meg to make sure their escape is ready for tomorrow. It’d be too suspicious to leave now and with the lockdown, impossible.

It had to be tomorrow, no matter how much Dean wanted to leave now. Of course, he'd thought about cashing in his last favour to let him go for the murder but he had a feeling that Lilith will be the least of his problems soon enough.

Anael appears at his cell door, practically a sight for sore eyes. She goes in, shutting the cell behind her. “I got rid of all the security footage. What the fuck were you thinking, Dean? Killing Roman’s favourite toy?”

“My fucking mistake, okay? I freaked out!” Dean says defensively.

She sighs, pinching the bridge of her nose as she turns away. “We’ve been here for 6 days. Your dad and Lilith are dead. Michael was almost dead. It’s like death follows you around, Dean.”

“I know it does,” Dean mutters.

In an attempt to take some edge off between them, Gabriel cuts in, “Look, are you and Adam good to go?”

“Yes, I just came here to let you know what happened to the tapes,” Anael clarifies. “Adam already arranged it with Michael.”

“Thank you,” Gabriel says.

“Dean, I need to say something,” Anael says, looking back at him. “Naomi knows about me and Ruby. She wants me to give up everyone’s names.” Dean is about to protest when she holds up a finger, continuing. “I won’t. I never will, especially knowing how many of you will hunt down me and my girlfriend, so relax.” Dean loses some tension in his face but Gabriel still looks a little on edge at the information.

Dean nods. “I appreciate that.”

“But don’t mistake this for kindness,” Anael says. “It’s purely out of obligation. Thank you for everything you’ve done for all of us the past few years but the moment we part ways tomorrow, I don’t want to see any of you ever again.”

Dean draws in a breath but nods anyway. “Okay. We’re done once we’re out.”

“Despite all that,” Anael says. “I really do respect you, Kansas. It was an honour to be a Dalí with you.”

Gabriel agrees. “Yeah. You know, it wasn’t always fun, especially when Cassie got shot in the first one, but you’re a genius, Dean. I’m glad I got to do this with you too.”

“Nobody else I’d rather do it with,” Dean says, trying for a weak smile. “Thank you for letting me be your Kansas.”

**Saturday, 7:13 PM**  
**131 hours**

Something about this feels like Adam’s seen this on Santa Clarita Diet, trying to hide a body. The only difference is that Dean is Sheila and the rest of them are Joel.

Michael paid off someone at the hospital’s mortuary to take Lilith’s body and dispose of it properly so the responsibility would be taken off of Adam and Anael’s hands. Even so, the place where the diener will meet them and take Lilith from them is still quite a distance from the prison.

At least it’s dark out, the roads are empty and the prison has vans.

“You know what?” Anael suddenly says as they pulled up in the meet-up spot at the hospital’s back door. “I didn’t think Dean had it in him to do that so good for him.”

“Good for him? An _officer_ is dead!” Adam reminds, bewildered.

“I know, her body’s behind us,” Anael says, rolling her eyes. “Look, Adam, I know this is a setback for the plan but she’s dead now. Nothing we can do about that. I’m not in Dean’s fan club but I think it’s safe to say that he only did this because he cares about you. She was gonna hurt you, he reacted. That’s all.”

Adam falls silent and looks out of the window before straightening up. “I see him.”

The diener, Ezekiel, stands by the door waiting for them as they slow to a stop in front of him. They both get out of the van and Anael says, her thumb pointing over her shoulder at the van, “Body’s in the back.”

“I got it,” Ezekiel nods. “Michael promised a million for this, right?”

“Two if you don’t document this,” Adam promises. “We’ll wire you the money tomorrow, okay?”

“You have a deal.”

**Saturday, 10:42 PM**  
**134 hours**

“De Luca."

Dean sits up in his bed and squints into the darkness outside his cell, seeing a silhouette that he knew all too well. “Cas?”

“Dean, how are you doing now?” Cas asks once the distance between them is smaller.

“Could be better, not gonna lie,” Dean says. “But it’ll be over soon so it can’t get any worse.”

Cas looks around, making sure nobody is around before his hand passes between the bars to gently pull Dean’s face a little closer so he can press a quick kiss to his lips. “I love you.”

“I love you too, Cas. I promise, once we’re out, I’m leaving this life behind. We’ll never do anything like this again.”

“And you’re gonna be the one to tell Sam and Jess.”

Dean sighs, hanging his head. “I will. Do you think we can leave out the bit about Lilith?”

Cas considers it. “I don’t think it’d hurt for them to not know that tiny detail.”

“Then I’ll tell them once we fly back to Italy,” Dean promises. “Goodnight, Cas.”

Cas intertwines their fingers together and whispers, “Goodnight.” He turns to leave but then stops, looking back. “Dean?”

“Yeah, baby?”

“When I look at you, I don’t see Kansas,” Cas says. “I just see Dean Winchester.”


	7. Day 7: Kansas

**Notes for the Chapter:**

> CW //
> 
> Mention of an overdose in the last section (doesn't actually happen)

**17 years ago**

“If you can’t hear a bullet you’re seein’, chances are it’s coming your way.”

It was the last piece of advice Bobby had given to Dean, one of many tidbits of wisdom he’d imparted onto Dean before he passed away, finding his demise in a heist gone wrong. Ellen has spent so much time with Sam and Jo, providing comfort however she could. Raising three kids on her own is no easy feat, especially when all of them had a trauma of some kind.

Back when John was still around, Dean had been taught to not be emotional. It made you vulnerable which made you weak which made you easy to kill. Dean lived by it, though now that he’s older, he sees the flawed logic. Some of the best people Dean knows, feel the most.

Dean did his best work when he felt the most; that was, when he felt so horrible about how Sam would grow up that he decided to give up his freedom for Sammy's. When Dean turned 18, he packed what he needed and left Ellen's house as soon as he was sure everyone was asleep.

He got a cheap room at a motel under a name he'd seen at a cemetery he passed on the way there. He did odd jobs until he pooled enough money to rent a room in the apartment of a woman with three too many cats for Dean's preference. She passed away in her sleep when he turned 20 and he took the apartment for himself.

When that happened, his heist plans spread from his room to the rest of the house. Blueprints, post-its, diagrams, experiments laid all over the walls and any available surface. Contact numbers were stuck on a cork board for reference and labelled burner phones hung on the walls. He made friends with the biggest players of the underworld, doing terrible favours in exchange for supplies for the heist.

This will be Dean's masterpiece, done in honour of Bobby, done to ensure Sam will have a good future. The heist on the Bank of America.

When Dean turns 27, he gets high enough in the criminal underworld to buy police files off of the black market. He gets people, their names blacked out as per his request. His half-brother from Minnesota who was a fantastic shoplifter. Two impressive con-women, one American and one from Britain. Two more Englishmen, one being the most wanted man in the UK and the other being a small-time robber. A miner that used tunnels to rob. A talented redhead hacker who bypassed even NASA's security. A dark-haired robber with a track record from Hell. The jewel thief with eyes like diamonds and hair like coal.

It was the perfect team, their files worth every dollar Dean spent to get them.

It seemed like things were finally looking up. Dean picked out a name for himself, Kansas, and Dean Winchester was long forgotten.

**Sunday, 10:29 AM**  
**146 hours**

"Dean Winchester." Roman drops his pen onto his desk, his face drawing into one of disdain. "Why did you want to meet me?"

He strolls into the office, looking around the room. It looks exactly like the last time Dean was here, clearly Roman puts a lot of effort in keeping order in his office. "Just getting some last minute things in place."

Roman frowns in realisation. "You're leaving today."

"Yup." Dean smiles. "I wanted to make sure we're both aware I still have one favour left."

"You do," Roman affirms, leaning into his chair. "Are you going to use it now?"

"Not yet. At some point, I will, but not yet," Dean denies.

Roman nods, looking mildly annoyed. "I'm tempted to ask you what tricks you have up your sleeve but you won't tell me, will you?"

"Nope."

Roman shrugs like he expected that answer. "Fine. Know that my guards will still follow protocol when you do attempt your break-out and that I will not stop the FBI agent from doing her job. Be aware that she will be here all day and will likely be here when you try to leave."

Dean already knew all of that. They might be able to dodge the correctional officers but he knew Naomi would probably catch them as they're going. He knows every Dalí in the prison, including himself, is more than willing to kill her.

Dean nods anyway. "I know."

"And another thing," Roman says. "Lilith Monroe."

He draws in a deep breath. "I killed her on accident."

"On accident," Roman echoes, eyebrows raised, incredulous.

"She was going to kill my brother, the nurse," Dean explains. "If that happened, his husband will kill me, my husband _and_ her."

Roman eyes him warily and finally sighs. "Well, at least Lilith is replaceable. She's no big loss, though the investigation will have to continue. I'll destroy anything that can connect it to you." He glances at the clock and mutters under his breath before he says, "I'll be waiting for that final favour to be used up. I'm assuming that you're retiring after this? It seems like the logical thing to do after pulling off three crimes this big."

Dean nods again.

Roman admits reluctantly, "Then before you go, I want to let you know that you must be the most impressive criminal I have ever had the pleasure to know."

Dean is somewhat surprised by the sentiment but he says, "Thanks."

"Now go," Roman dismisses, flapping a hand in the direction of the door. "Good luck."

**1 year ago**

“Like we practised, Cas. Don’t look back.”

“Dean, this is ridiculous,” Cas says, looking over his shoulder to peek at Dean.

Dean flashes him a grin. "Hey. You know it won't work if you look back."

“I fail to see why me looking away is such a big factor,” Cas says flatly, though he does turn back around to face away from Dean. He hears some rustling behind him and then, quietly:

“Surprise.”

Cas turns; Dean is gone. “What the hell are you doing? Where are you hiding?” He suddenly feels hands rest on his shoulders and he twists around, eyes wide, to be greeted by the Dalí mask. “Why are you wearing that?”

“Come on, you don’t miss me even a little bit?” Kansas asks, sitting back down. “Your commander.”

“I’d rather not be living in fear as trained military assassins played cat and mouse with us, thank you,” Cas says dryly, though his fingertips gently caressed the material of the mask. “But Kansas was truly something else. I didn’t miss the terror but I do miss working with you.” Cas gets up so he’s now kneeling and, putting a hand on one of Dean’s shoulders for support, he leans forward to press a kiss to the mask’s cheek. “I think it’s better for the both of us if you didn’t come back again, as much as it hurts me to say it.”

Kansas’s hand reaches up to rest over Cas’s. “Really?”

“Really,” Cas says. “No offence, but nothing good happens when Kansas is around.”

“Say that to all the money you earned.”

“Maybe one good thing happened.” Cas shrugs. “But Kansas is better off in storage.” Cas pulls the mask off to see Dean’s soft smile. “Or two. I like Dean better.”

**Sunday, 2:02 PM**  
**150 hours**

Crowley is astounded and frankly impressed. Dean told them all that they would be leaving within the hour and Crowley can't believe he managed to get him off death row. It's a difficult feat and Dean did it in a week without Naomi discovering him or any of the others without the informant.

Kansas is truly a force to be reckoned with, for sure. Constantly achieving the impossible. He'd robbed America and London blind and they let him get away with it.

Naomi had given up on interrogating him today so he'd taken his lunch to the prison's chapel to spend the time with Castiel, Adam and Anael. Gabriel and Dean were in the cafeteria, handling the food. Crowley _should_ be there but it's the one time the kitchen staff isn't aware that he's free so why not use his last day in prison doing whatever the fuck he wants?

"What will you do after we get out of here?" Adam asks conversationally, texting Michael — planning what they'll do the moment he's out of the prison doors.

"Probably propose to Ruby," Anael mumbles, looking down at her blood red nails. "I think it's time, right?"

Castiel looks up at her from his place on the benches, giving her a faint smile. "Congratulations in advance."

"Thanks, Cas," Anael grins. "And the rest of you?"

"Back to Detroit," Adam says, eyes still glued to his phone. "Or maybe we'll move."

"Where to?" Crowley asks half-heartedly.

Adam gives him a flat look. "If we did move, I wouldn't tell you."

Crowley huffs in annoyance and continues talking, "Back to the UK. I'll be laying low for a bit but I don't think I can bring myself to stop being a criminal. What about you, kleptomaniac?"

"I think I'll lead a quiet life," Cas says lightly. "My family is intact. What I have is enough."

"Fair enough," Adam agrees. "So Crowley's gonna be the only one going on?"

Crowley hesitates. "It's still up for debate."

Anael laughs. "I think the Dalís just died."

A little over half an hour later, they're in the kitchen waiting for Dorothy, Meg, Mick and Jo to arrive with the truck to get them out. Adam, Anael and Cas were still there just to make sure everything goes smoothly.

"Where the hell are they?" Gabriel mumbles, squinting to look out for the truck.

"Meg says they took the produce truck," Dean notifies.

"I see it," Cas says, pointing ahead at the approaching truck.

Anael breaks into a smile. "This is it."

The truck pulls up and the backdoors open to reveal Meg and Mick. Mick gestures for them to get in, saying, "Come on, we don't have a lot of time. Someone fucked up—"

Meg hisses, "Davies, now is not the—"

Crowley freezes, halfway onto the truck, and voices what everyone else is thinking, "Davies, you better tell us what went wrong." Mick glares at Meg and she sighs, frustrated. When she opens her mouth to explain, they hear cars rolling up nearby and Dean curses under his breath, moving over to check what it is.

At least five cars with FBI agents pouring out of them. So much for Roman's wish of good luck. "Fuck."

"Dean, what?" Adam asks, tense.

“We can’t get out,” Dean mutters, eyes wide. “There're too many cops out there, we can’t even try to fight our way out without killing anyone.”

Cas’s face pales slightly and he looks back to look back at the others. “How did they even know we would be leaving right now?”

Dean exhales sharply, frustrated. “I don’t know. Maybe Davies ratted us out. He used to be a cop, after all.”

Mick protests, "After how deep I am in this? I'd be incriminating myself! No!"

"Someone gave up my name and Michael's!" Anael snaps, impatient. " _Own the fuck up._ "

“Davies didn’t rat you out,” Meg says, exasperated.

“ _Then who did?_ ” Cas questions, beginning to feel anger under his skin.

“ _I did._ ”

Dean realises it; that ticking time bomb has finally gone off — Meg Masters. His voice is quiet when he asks, “Why?”

“Don’t get me wrong, I’m grateful for the loot you got us but face it, Dean. As long as you’re still walking around out there, this nightmare will never end. Crowley would have been dead in a week. Naomi threatened Anael and her girlfriend. Lilith almost got Adam yesterday,” Meg points out, desperate for Dean to see her point. “Abaddon hunted us down one by one and we lost Balthazar, Bela and Benny. Bevell shot you. We almost lost Michael twice. You were lost for a few minutes too, don’t forget. This time, you walk right into prison with cuffs around your hands and expected to get away?”

“I’ve done it before,” Dean says, feeling red hot anger in his body.

“You got lucky,” Meg corrects. “Nobody gets lucky twice.”

Anael cuts in, “Meg, seriously, you don’t expect us all to surrender, right? I’m not exactly in Dean’s corner either but if you think I’m going to walk out there and tell them to arrest me just so you can get back at Dean, you’re wrong. Don’t make me show you just how wrong.”

Meg nods slowly before explaining, “I cut a deal with that FBI agent, Naomi.”

Adam pauses. “What deal?”

“I bargained with her for a long time and we came to a compromise. Naomi only really wants the head honcho, the mastermind,” Meg clarifies. “The rest of us can go as long as we don’t do any more crime.”

Gabriel’s eyes widen slightly, confused. “That cannot be legal. No way she’s just gonna let us go.”

“She sent MI6 and Black Ops to kill us and agreed to cover both up as rogue agents, you think she cares what’s legal or not? She’ll just say we gave her the slip and got away, then burn our files,” Meg says. “So the deal is this — Dean, you give yourself up right now and the rest of us are free. Me, Crowley, Anael, Gabriel, Mick, Rowena, Eileen, Charlie, Dorothy, Ash, Jo, those two twins who helped bust me out the first heist. Michael, Jess, Adam. Cas and Sam. They get to go free.”

That gets Dean thinking. His freedom for everyone else's seems like a fair trade, considering that he was the one to get them into this mess.

Cas turns to him, bewildered. “You cannot possibly be thinking about this.”

“Cas, baby, I don’t have a choice—“

“You have a choice!”

“Not when it comes to you!” Dean cuts in. “ _I love you_ , Cas. And if getting caught means you and my family get to go free then I’m doing it, no question.”

Dorothy gives them a tense look from the front of the truck. "Guys, we're running out of time. We need to go right now. I'm sorry."

Meg is already getting Crowley on the truck — Anael and Adam leave through a regular exit, out of Naomi's sight. Gabriel touches a hand to Cas's arm gently. "Cassie, we gotta go. We're running out of time."

Cas stammers, "No, but Dean, he—"

" _Go_ ," Dean insists. "I'll come back soon, promise. I've got a plan."

"I don't care if you have a plan. How am I supposed to leave you here alone?" Cas asks, desperate to stay.

“Just like we practised, Cas,” Dean says with a pleading smile as Gabriel makes him move. “Don’t look back. I love you.”

"Dean!" Cas protests but Gabriel manages to get him back into the prison so he can leave and Dean looks back at the door. Knowing how many cops are out there is a bit intimidating but he's walked right into a cop tent before and he'd been fearless. He just needs to be Kansas one more time.

Cas turns; Dean is gone. Kansas doesn’t look back at him.

Kansas opens the door and walks right out, seeing Naomi arriving just in time to see him. Every rifle in the vicinity is pointed right at him. _If you can’t hear a bullet you’re seein’, chances are it’s coming your way._ All the guns are silent, no triggers pulled, but Kansas feels like all the bullets are emptied out on him.

Opening his arms wide as if presenting himself, he gives them the same smile he always showed his hostages.

“I’m Kansas, the mastermind of the heist of the Bank of America and the Diamonds Factory. My name is Dean Winchester.”

“Dean Winchester, you are under arrest.”

**6 months later**

**Palermo, Italy**

Two months after Missouri, Sam had finally found it in himself to forgive everyone involved. Anael kept to her wishes, cutting contact from almost every Dalí. As far as Cas knew, she was still friends with him, Jess, Michael, Adam, Rowena, Eileen, Charlie and Dorothy. Michael and Adam flew back to Detroit where Cas hasn't heard from them since. Mick and Meg went radio silent as well, likely out of guilt for selling Dean out. Crowley is still in contact with them; Cas thinks it's out of obligation that they saved him from the electric chair.

Five months after, Palermo still feels just as lonely even with Sam and Jess to keep Cas company. He still missed Dean just as much. He'd had a message passed on to him from Alfie a month after, when the kid had been released, from Dean — that he would be back to him as soon as possible and to not visit him for his own safety.

Cas was reluctant but knew that the impulsive decision to go back for Dean will get them both in deeper trouble than they've found themselves in. There was no good outcome for it.

So Cas did wait. He'd stopped stealing jewels, something his kleptomania argued with, but eventually he learned to forget the habit. He busied his hands with origami instead, an activity he does with Jess. They draped paper cranes from the ceiling of his and Dean's bedroom, something Cas hoped will be a welcome sight for Dean when he returns.

Six months and three days after, someone knocks on his front door. Cas doesn't think anything of it, shouting to the person as he turns down the heat on his stove, "Give me a second, I'll be right there!"

"Take your time, baby!"

Cas shuts off the heat and runs to the door, fiddling with the lock in frustration until he gets it, throwing open the door to see Dean's tired smile. He has a bruise on one cheek, still shiny, and a cut lip that leads Cas to notice that he now has a stubble. His hair is a bit longer and unkempt and the clothes he's wearing are obviously not his.

Despite it all, he still looks like home.

"Dean," Cas barely utters. "You came back."

"I told you I'd come home." Dean grins and Cas practically collapses in his arms with relief. "I missed you."

"How did you do it?" Cas asks, pulling away to give Dean a once-over, assessing any damage. "You had a life sentence. Did you make a deal with that FBI agent—"

" _No_ , no," Dean quickly denies. "Nothing like that. When we were there the first time, my fourth favour was that if things went south and I got caught, I'd be sent to his prison. Roman bargained with Naomi and managed to do that. I stayed there for half a year to make sure Naomi's guard was down. I knew they were watching me because I broke Crowley out. I would have come back sooner if there weren't any eyes on me. So I waited it out and 6 months later, I walked into Roman's office and cashed in my last favour."

Cas puts the pieces together. "Your release."

“Bingo.” Dean closes the door behind him and takes a seat at the table, looking back up at Cas. “I’m officially legally dead again. Roman handled the documents, said I overdosed on Alastair’s heroin. His people snuck me out of the prison and we paid off someone at the hospital to fake the autopsy records.”

Cas sits down heavily, his face in awe. "We're free."

"We're free," Dean affirms. "And Cas? I promise you that's the last time I'll ever do anything like that again."

He checks, "You won't solve anyone's problems?"

Dean nods. "Unless you want me to, it's none of my business anymore. Well, I will help Sam and Adam if they want me to help, of course, but that's it."

"You'll live a quiet life with me?"

"Well..." Dean leans over to press a gentle kiss to Cas's lips. "Dead people are supposed to be quiet, right?"

Cas grins against Dean's mouth. "Right."

"I'm right here," Dean murmurs by Cas's ear. "Kansas is dead."

"I did always like Dean better anyway," Cas whispers, pulling Dean in for another kiss, the first of many that followed them into their life of quiet. The next morning, they invited Sam and Jess to come with them as they all drowned their Dalí masks in the sea.

Dean picked up a job as a bartender in a nightclub near their home and Cas ended up becoming a diamond consultant at a jewellery shop like Michael. Though Adam and Michael didn't keep up with Dean anymore, he'd heard from old contacts that Michael didn't go down the business route after all and stayed in the jewel business. Whatever bits of information from the other robbers he got, it seemed like almost none of them did crime anymore.

A year after Missouri, Anael had mailed an invite to Dean and Cas to her wedding with Ruby, writing on the blank side of the card that it seemed wrong to not invite them after everything they went through together. Their wedding was the last time Dean ever saw all the surviving Dalís in one spot and it felt like the ones they lost were there with them too. Meg brought a Spanish girl who cheats at casinos with her to the wedding — she looks like Bela.

A year and a half after prison, Sam and Jess have a daughter. They name her Clara, after Santa Clara where they met in Stanford. Dean tells them that Jess's code name Madrid would have been a good contender for a name — Sam throws a shoe at him and jokes that Kansas would be a terrible name for their kid. Cas says Angeles is a good one and Jess wholeheartedly agreed, then they all realised they barely remember what city names some of the other Dalís chose.

It didn't matter to Dean anymore; he didn't need the mask or the city name. He knows exactly who he is now.

The man who pulled off the two greatest heists in history and broke the United Kingdom's most wanted criminal out of death row — Dean Winchester.

**Notes for the Chapter:**

> Thanks for following this series! I hope it was enjoyable, at least.
> 
> Again, the 3 parts were inspired by La Casa De Papel and Vis à Vis, so if you haven't seen them but you liked these, I think you'd like the shows too! Forewarning for mature content, especially from Vis à Vis.


End file.
